Chemical compounds

ABSTRACT

The use of a compound of formula I 
     
       
         
         
             
             
         
       
         
         
           
             Y is a single bond, C═O, C═S or S(O) m  where m is 0, 1 or 2; the ring 
           
         
       
    
     
       
         
         
             
             
         
       
     
     is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring;
         Z and Z′ are       

     
       
         
         
             
             
         
       
     
     provided that both are not N; R 1 , R 2 , R 3 , R 3a , R 4 , R 8  and Ra are specified organic groups and n and p are independently 0, 1, 2, 3 or 4; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs. Novel compounds are also provided.

This application is a divisional application of U.S. Ser. No. 11/571,303filed Apr. 27, 2006, which is a 371 of International Application No.PCT/IB2005/002002 filed Jun. 22, 2005, which claims priority to GB0414438.2 filed Jun. 28, 2004, the contents of which are incorporatedherein by reference.

The present invention relates to piperidine derivatives, to processesfor preparing them, to insecticidal, acaricidal, molluscicidal andnematicidal compositions comprising them and to methods of using them tocombat and control insect, acarine, mollusc and nematode pests.

Piperidine derivatives with fungicidal properties are disclosed in forexample in EP494717.

It has now surprisingly been found that certain piperidines haveinsecticidal properties.

The present invention therefore provides a method of combating andcontrolling insects, acarines, nematodes or molluscs which comprisesapplying to a pest, to a locus of a pest, or to a plant susceptible toattack by a pest an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I):

Y is a single bond, C═O, C═S or S(O)_(m) where m is 0, 1 or 2;

the ring

is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromaticring;

Z and Z′ are joined by a single or a double bond and are

provided that both are not N;

R¹ is hydrogen, optionally substituted alkyl, optionally substitutedalkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl,optionally substituted alkylaminocarbonyl, optionally substituteddialkylaminocarbonyl, optionally substituted aryl, optionallysubstituted heteroaryl, optionally substituted alkoxy, optionallysubstituted aryloxy, optionally substituted heteroaryloxy, optionallysubstituted heterocyclyloxy, cyano, optionally substituted alkenyl,optionally substituted alkynyl, optionally substituted cycloalkyl,optionally substituted cycloalkenyl, formyl, optionally substitutedheterocyclyl, optionally substituted alkylthio, NO or NR¹³R¹⁴ where R¹³and R¹⁴ are independently hydrogen, COR¹⁵, optionally substituted alkyl,optionally substituted aryl, optionally substituted heteroaryl,optionally substituted heterocyclyl or R¹³ and R¹⁴ together with the NR¹⁴ atom to which they are attached form a group —N═C(R¹⁶)—NR¹⁷R¹⁸ orR¹³ and together with the N atom to which they are attached form a five,six or seven-membered heterocyclic ring which may contain one or twofurther heteroatoms selected from O, N or S and which may be optionallysubstituted by one or two C₁₋₆ alkyl groups; R¹⁵ is H, optionallysubstituted alkyl, optionally substituted alkoxy, optionally substitutedaryl, optionally substituted aryloxy optionally substituted heteroaryl,optionally substituted heteroaryloxy or NR¹⁹R²⁰; R¹⁶, R¹⁷ and R¹⁸ areeach independently H or lower alkyl; R¹⁹ and R²⁰ are independentlyoptionally substituted alkyl, optionally substituted aryl or optionallysubstituted heteroaryl;

R² is H, hydroxy, optionally substituted alkoxy or optionallysubstituted alkyl; or R¹ and R² together with the groups Y and N form a5- or 6-membered heterocyclic ring which may optionally contain onefurther heteroatom selected from O, N or S and which may be optionallysubstituted by C₁₋₄ alkyl, C₁₋₄ haloalkyl or halogen;

R³ is H, OH, halogen or optionally substituted alkyl;

R^(3a) is H or R³ and R^(3a) together form a bond;

each R⁴ is independently halogen, nitro, cyano, optionally substitutedC₁₋₈ alkyl, optionally substituted C₂₋₆ alkenyl, optionally substitutedC₂₋₆ alkynyl, optionally substituted alkoxycarbonyl, optionallysubstituted alkylcarbonyl, optionally substituted alkylaminocarbonyl,optionally substituted dialkylaminocarbonyl, optionally substituted C₃₋₇cycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, optionally substituted heterocyclyl, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitutedheteroaryloxy, optionally substituted alkylthio or R²¹R²²N where R²¹ andR²² are, independently, hydrogen, C₁₋₈ alkyl, C₃₋₇ cycloalkyl, C₃₋₆alkenyl, C₃₋₆ alkynyl, C₃₋₇ cycloalkyl(C₁₋₄alkyl, C₂₋₆ haloalkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, C₁₋₆ alkoxycarbonyl or R²¹ and R²² together with theN atom to which they are attached form a five, six or seven-memberedheterocyclic ring which may contain one or two further heteroatomsselected from O, N or S and which may be optionally substituted by oneor two C₁₋₆ alkyl groups, or 2 adjacent groups R⁴ together with thecarbon atoms to which they are attached form a 4, 5, 6, or 7 memberedcarbocyclic or heterocyclic ring which may be optionally substituted byhalogen; n is 0, 1, 2, 3 or 4;

R⁸ is optionally substituted alkyl, optionally substituted alkenyl,optionally substituted alkynyl, optionally substituted cycloalkyl,optionally substituted aryl, optionally substituted alkoxy, optionallysubstituted aryloxy, optionally substituted alkoxycarbonyl, optionallysubstituted alkylcarbonyl or optionally substituted alkenylcarbonyl;

each Ra is independently halogen, hydroxy, cyano, optionally substitutedC₁₋₈ alkyl, optionally substituted C₂₋₆ alkenyl, optionally substitutedC₂₋₆ alkynyl, optionally substituted alkoxycarbonyl, optionallysubstituted alkylcarbonyl, optionally substituted alkylaminocarbonyl,optionally substituted dialkylaminocarbonyl, optionally substituted C₃₋₇cycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, optionally substituted heterocyclyl, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitutedheteroaryloxy, optionally substituted alkylthio, optionally substitutedarylthio or R²³R²⁴N where R²³ and R²⁴ are, independently, hydrogen, C₁₋₈alkyl, C₃₋₇ cycloalkyl, C₃₋₆ alkenyl, C₃₋₆ alkynyl, C₃₋₇cycloalkyl(C₁₋₄alkyl, C₂₋₆ haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₁₋₆alkoxycarbonyl or R²³ and R²⁴ together with the N atom to which they areattached form a five, six or seven-membered heterocyclic ring which maycontain one or two further heteroatoms selected from O, N or S and whichmay be optionally substituted by one or two C₁₋₆ alkyl groups, or two Ragroups attached to the same carbon atom are ═O, ═S, ═NRb, ═CRcRd whereRb, Rc and Rd are independently H or optionally substituted alkyl; p is0, 1, 2, 3 or 4 or salts or N-oxides thereof.

The compounds of formula (I) may exist in different geometric or opticalisomers or tautomeric forms. This invention covers all such isomers andtautomers and mixtures thereof in all proportions as well as isotopicforms such as deuterated compounds.

Each alkyl moiety either alone or as part of a larger group (such asalkoxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl) is a straight or branched chain and is, forexample, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl,iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or neo-pentyl. Thealkyl groups are suitably C₁ to C₁₂ alkyl groups, but are preferablyC₁-C₁₀, more preferably C₁-C₈, even more preferably preferably C₁-C₆ andmost preferably C₁-C₄ alkyl groups.

When present, the optional substituents on an alkyl moiety (alone or aspart of a larger group such as alkoxy, alkoxycarbonyl, alkylcarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl) include one or more ofhalogen, nitro, cyano, NCS—, C₃₋₇ cycloalkyl (itself optionallysubstituted with C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl (itselfoptionally substituted with C₁₋₆ alkyl or halogen), hydroxy, C₁₋₁₀alkoxy, C₁₋₁₀ alkoxy(C₁₋₁₀)alkoxy, tri(C₁₋₄)alkylsilyl(C₁₋₆)alkoxy, C₁₋₆alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀ haloalkoxy, aryl(C₁₋₄)-alkoxy (wherethe aryl group is optionally substituted), C₃₋₇ cycloalkyloxy (where thecycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen),C₂₋₁₀ alkenyloxy, C₂₋₁₀ alkynyloxy, SH, C₁₋₁₀ alkylthio, C₁₋₁₀haloalkylthio, aryl(C₁₋₄)alkylthio (where the aryl group is optionallysubstituted), C₃₋₇ cycloalkylthio (where the cycloalkyl group isoptionally substituted with C₁₋₆ alkyl or halogen),tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, arylthio (where the aryl group isoptionally substituted), C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl,C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, arylsulfonyl (where the arylgroup may be optionally substituted), tri(C₁₋₄)alkylsilyl,aryldi(C₁₋₄)alkylsilyl, (C₁₋₄alkyldiarylsilyl, triarylsilyl, C₁₋₁₀alkylcarbonyl, HO₂C, C₁₋₁₀ alkoxycarbonyl, aminocarbonyl, C₁₋₆alkylaminocarbonyl, di(C₁₋₆ alkyl)aminocarbonyl, N—(C₁₋₃ alkyl)-N—(C₁₋₃alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy, arylcarbonyloxy (where thearyl group is optionally substituted), di(C₁₋₆)alkylaminocarbonyloxy,oximes such as ═NOalkyl, ═NOhaloalkyl and ═NOaryl (itself optionallysubstituted), aryl (itself optionally substituted), heteroaryl (itselfoptionally substituted), heterocyclyl (itself optionally substitutedwith C₁₋₆ alkyl or halogen), aryloxy (where the aryl group is optionallysubstituted), heteroaryloxy, (where the heteroaryl group is optionallysubstituted), heterocyclyloxy (where the heterocyclyl group isoptionally substituted with C₁₋₆ alkyl or halogen), amino, C₁₋₆alkylamino, di(C₁₋₆)alkylamino, C₁₋₆ alkylcarbonylamino,N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino, C₂₋₆ alkenylcarbonyl, C₂₋₆alkynylcarbonyl, C₃₋₆ alkenyloxycarbonyl, C₃₋₆ alkynyloxycarbonyl,aryloxycarbonyl (where the aryl group is optionally substituted) andarylcarbonyl (where the aryl group is optionally substituted).

Alkenyl and alkynyl moieties can be in the form of straight or branchedchains, and the alkenyl moieties, where appropriate, can be of eitherthe (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.

When present, the optional substituents on alkenyl or alkynyl includethose optional substituents given above for an alkyl moiety.

In the context of this specification acyl is optionally substituted C₁₋₆alkylcarbonyl (for example acetyl), optionally substituted C₂₋₆alkenylcarbonyl, optionally substituted C₂₋₆ alkynylcarbonyl, optionallysubstituted arylcarbonyl (for example benzoyl) or optionally substitutedheteroarylcarbonyl.

Halogen is fluorine, chlorine, bromine or iodine.

Haloalkyl groups are alkyl groups which are substituted with one or moreof the same or different halogen atoms and are, for example, CF₃, CF₂Cl,CF₃CH₂ or CHF₂CH₂.

In the context of the present specification the terms “aryl”, “aromaticring” and “aromatic ring system” refer to ring systems which may bemono-, bi- or tricyclic. Examples of such rings include phenyl,naphthalenyl, anthracenyl, indenyl or phenanthrenyl. A preferred arylgroup is phenyl. In addition, the terms “heteroaryl”, “heteroaromaticring” or “heteroaromatic ring system” refer to an aromatic ring systemcontaining at least one heteroatom and consisting either of a singlering or of two or more fused rings. Preferably, single rings willcontain up to three and bicyclic systems up to four heteroatoms whichwill preferably be chosen from nitrogen, oxygen and sulphur. Examples ofsuch groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl,indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl,benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazolequinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl andindolizinyl. Preferred examples of heteroaromatic radicals includepyridyl, pyrimidyl, triazinyl, thienyl, furyl, oxazolyl, isoxazolyl,2,1,3-benzoxadiazole and thiazolyl.

The terms heterocycle and heterocyclyl refer to a non-aromatic ringcontaining up to 10 atoms including one or more (preferably one or two)heteroatoms selected from O, S and N. Examples of such rings include1,3-dioxolane, tetrahydrofuran and morpholine.

When present, the optional substituents on heterocyclyl include C₁₋₆alkyl and C₁₋₆ haloalkyl as well as those optional substituents givenabove for an alkyl moiety.

Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.

Cycloalkenyl includes cyclopentenyl and cyclohexenyl.

When present, the optional substituents on cycloalkyl or cycloalkenylinclude C₁₋₃ alkyl as well as those optional substituents given abovefor an alkyl moiety.

Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.

When present, the optional substituents on aryl or heteroaryl areselected independently, from halogen, nitro, cyano, NCS—, C₁₋₆ alkyl,C₁₋₆ haloalkyl, C₁₋₆ alkoxy-(C₁₋₆)alkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl,C₂₋₆ alkynyl, C₃₋₇ cycloalkyl (itself optionally substituted with C₁₋₆alkyl or halogen), C₅₋₇ cycloalkenyl (itself optionally substituted withC₁₋₆ alkyl or halogen), hydroxy, C₁₋₁₀ alkoxy, C₁₋₁₀alkoxy(C₁₋₁₀)alkoxy, tri(C₁₋₄)alkyl-silyl(C₁₋₆)alkoxy, C₁₋₆alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀ haloalkoxy, aryl(C₁₋₄)alkoxy (wherethe aryl group is optionally substituted with halogen or C₁₋₆ alkyl),C₃₋₇ cycloalkyloxy (where the cycloalkyl group is optionally substitutedwith C₁₋₆ alkyl or halogen), C₂₋₁₀ alkenyloxy, C₂₋₁₀ alkynyloxy, SH,C₁₋₁₀ alkylthio, C₁₋₁₀ haloalkylthio, aryl(C₁₋₄)alkylthio C₃₋₇cycloalkylthio (where the cycloalkyl group is optionally substitutedwith C₁₋₆ alkyl or halogen), tri(C₁₋₄-alkylsilyl(C₁₋₆)alkylthio,arylthio, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, arylsulfonyl,tri(C₁₋₄)alkylsilyl, aryldi(C₁₋₄)-alkylsilyl, (C₁₋₄alkyldiarylsilyl,triarylsilyl, C₁₋₁₀ alkylcarbonyl, HO₂C, C₁₋₁₀ alkoxycarbonyl,aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆ alkyl)-aminocarbonyl,N—(C₁₋₃ alkyl)-N—(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy,arylcarbonyloxy, di(C₁₋₆)alkylamino-carbonyloxy, aryl (itself optionallysubstituted with C₁₋₆ alkyl or halogen), heteroaryl (itself optionallysubstituted with C₁₋₆ alkyl or halogen), heterocyclyl (itself optionallysubstituted with C₁₋₆ alkyl or halogen), aryloxy (where the aryl groupis optionally substituted with C₁₋₆ alkyl or halogen), heteroaryloxy(where the heteroaryl group is optionally substituted with C₁₋₆ alkyl orhalogen), heterocyclyloxy (where the heterocyclyl group is optionallysubstituted with C₁₋₆ alkyl or halogen), amino, C₁₋₆ alkylamino,di(C₁₋₆)alkylamino, C₁₋₆ alkylcarbonylamino,N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino, arylcarbonyl, (where the arylgroup is itself optionally substituted with halogen or C₁₋₆ alkyl) ortwo adjacent positions on an aryl or heteroaryl system may be cyclisedto form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itselfoptionally substituted with halogen or C₁₋₆ alkyl. Further substituentsfor aryl or heteroaryl include aryl carbonyl amino (where the aryl groupis substituted by C₁₋₆ alkyl or halogen), (C₁₋₆)alkyloxycarbonylamino(C₁₋₆)alkyloxycarbonyl-N—(C₁₋₆)alkylamino, aryloxycarbonylamino (wherethe aryl group is substituted by C₁₋₆ alkyl or halogen),aryloxycarbonyl-N—(C₁₋₆)alkylamino, (where the aryl group is substitutedby C₁₋₆ alkyl or halogen), arylsulphonylamino (where the aryl group issubstituted by C₁₋₆ alkyl or halogen), arylsulphonyl-N—(C₁₋₆)alkylamino(where the aryl group is substituted by C₁₋₆ alkyl or halogen),aryl-N—(C₁₋₆)alkylamino (where the aryl group is substituted by C₁₋₆alkyl or halogen), arylamino (where the aryl group is substituted byC₁₋₆ alkyl or halogen), heteroaryl amino (where the heteroaryl group issubstituted by C₁₋₆ alkyl or halogen), heterocyclylamino (where theheterocyclyl group is substituted by C₁₋₆ alkyl or halogen),aminocarbonylamino, C₁₋₆ alkylaminocarbonyl amino,di(C₁₋₆)alkylaminocarbonyl amino, arylaminocarbonyl amino where the arylgroup is substituted by C₁₋₆ alkyl or halogen),aryl-N—(C₁₋₆)alkylaminocarbonylamino where the aryl group is substitutedby C₁₋₆ alkyl or halogen), C₁₋₆ alkylaminocarbonyl-N—(C₁₋₆)alkyl amino,di(C₁₋₆)alkylaminocarbonyl-N—(C₁₋₆)alkyl amino,arylaminocarbonyl-N—(C₁₋₆)alkyl amino where the aryl group issubstituted by C₁₋₆ alkyl or halogen) andaryl-N—(C₁₋₆)alkylaminocarbonyl-N—(C₁₋₆)alkyl amino where the aryl groupis substituted by C₁₋₆ alkyl or halogen).

For substituted phenyl moieties, heterocyclyl and heteroaryl groups itis preferred that one or more substituents are independently selectedfrom halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆haloalkylsulfonyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₃₋₇cycloalkyl, nitro, cyano, CO₂H, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl,R²⁵R²⁶N or R²⁷R²⁸NC(O); wherein R²⁵, R²⁶, R²⁷ and R²⁸ are,independently, hydrogen or C₁₋₆ alkyl. Further preferred substituentsare aryl and heteroaryl groups.

Haloalkenyl groups are alkenyl groups which are substituted with one ormore of the same or different halogen atoms.

It is to be understood that dialkylamino substituents include thosewhere the dialkyl groups together with the N atom to which they areattached form a five, six or seven-membered heterocyclic ring which maycontain one or two further heteroatoms selected from O, N or S and whichis optionally substituted by one or two independently selected(C₁₋₆)alkyl groups. When heterocyclic rings are formed by joining twogroups on an N atom, the resulting rings are suitably pyrrolidine,piperidine, thiomorpholine and morpholine each of which may besubstituted by one or two independently selected (C₁₋₆) alkyl groups.

Preferably the optional substituents on an alkyl moiety include one ormore of halogen, nitro, cyano, HO₂C, C₁₋₁₀ alkoxy (itself optionallysubstituted by C₁₋₁₀ alkoxy), aryl(C₁₋₄)alkoxy, C₁₋₁₀ alkylthio, C₁₋₁₀alkylcarbonyl, C₁₋₁₀ alkoxycarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆alkyl)aminocarbonyl, (C₁₋₆)alkylcarbonyloxy, optionally substitutedphenyl, heteroaryl, aryloxy, arylcarbonyloxy, heteroaryloxy,heterocyclyl, heterocyclyloxy, C₃₋₇ cycloalkyl (itself optionallysubstituted with (C₁₋₆)alkyl or halogen), C₃₋₇ cycloalkyloxy, C₅₋₇cycloalkenyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl,tri(C₁₋₄)alkylsilyl, tri(C₁₋₄)alkylsilyl(C₁₋₆)alkoxy,aryldi(C₁₋₄)alkylsilyl, (C₁₋₄alkyldiarylsilyl and triarylsilyl.

Preferably the optional substituents on alkenyl or alkynyl include oneor more of halogen, aryl and C₃₋₇ cycloalkyl.

A preferred optional substituent for heterocyclyl is C₁₋₆ alkyl.

Preferably the optional substituents for cycloalkyl include halogen,cyano and C₁₋₃ alkyl.

Preferably the optional substituents for cycloalkenyl include C₁₋₃alkyl, halogen and cyano.

Preferred groups for T, Y, Ra, R¹, R², R³, R^(3a), R⁴ and R⁸ in anycombination thereof are set out below.

Preferably Y is a single bond, C═O or C═S.

More preferably Y is a single bond or C═O.

Most preferably Y is C═O.

Preferably R¹ is hydrogen, C₁₋₆ alkyl, C₁₋₆ cyanoalkyl, C₁₋₆ haloalkyl,C₃₋₇ cycloalkyl(C₁₋₄alkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, heteroaryl(C₁₋₆)alkyl(wherein the heteroaryl group may be optionally substituted by halo,nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy,C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆alkoxycarbonyl, C₁₋₆ alkylcarbonylamino, arylcarbonyl, or two adjacentpositions on the heteroaryl system may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen), aryl(C₁₋₆)alkyl (wherein the aryl group may be optionallysubstituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylcarbonylamino, arylcarbonyl,or two adjacent positions on the aryl system may be cyclised to form a5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionallysubstituted with halogen), C₁₋₆ alkylcarbonylamino(C₁₋₆)alkyl, aryl(which may be optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl,C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the arylsystem may be cyclised to form a 5, 6 or 7 membered carbocyclic orheterocyclic ring, itself optionally substituted with halogen),heteroaryl (which may be optionally substituted by halo, nitro, cyano,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl,C₁₋₆ alkylcarbonylamino, arylcarbonyl, or two adjacent positions on theheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen), C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, phenoxy (wherein the phenylgroup is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy,C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino), heteroaryloxy (optionally substituted by halo, nitro,cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy),heterocyclyloxy (optionally substituted by halo, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), cyano, C₂₋₆ alkenyl, C₂₋₆alkynyl, C₃₋₆ cycloalkyl, C₅₋₇ cycloalkenyl, heterocyclyl (optionallysubstituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy or C₁₋₆ haloalkoxy), C₁₋₆ alkylthio, C₁₋₆ haloalkylthio orNR¹³R¹⁴ where R¹³ and R¹⁴ are independently hydrogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, phenyl (which may be optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino, dialkylamino or C₁₋₄alkoxycarbonyl), phenyl(C₁₋₆)alkyl (wherein the phenyl group may beoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacentpositions on the phenyl ring may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen), heteroaryl(C₁₋₆)alkyl (wherein the heteroaryl group maybe optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆alkylcarbonylamino, arylcarbonyl, or two adjacent positions on theheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen) or heteroaryl (which may be optionally substituted by halo,nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆haloalkoxy, C₁₋₄ alkoxycarbonyl C₁₋₆ alkylcarbonylamino,phenyloxycarbonylamino (wherein the phenyl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino), amino,C₁₋₆ alkylamino or phenylamino (wherein the phenyl group is optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino)).

More preferably R¹ is C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, heteroaryl(C₁₋₃)alkyl (wherein the heteroaryl groupmay be optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkoxycarbonyl, or two adjacent positions on the heteroaryl system maybe cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclicring, itself optionally substituted with halogen), phenyl(C₁₋₃)alkyl(wherein the phenyl group may be optionally substituted by halogen, C₁₋₄alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl,heteroaryl, amino, dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆alkoxycarbonyl, or two adjacent positions on the phenyl ring may becyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring,itself optionally substituted with halogen), phenyl (which may beoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacentpositions on the phenyl ring may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen), heteroaryl (which may be optionally substituted by halo,nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy,C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacent positions onthe heteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen), C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₂₋₆ alkenyl, heterocyclyl(optionally substituted by halo, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy or C₁₋₆ haloalkoxy), C₁₋₆ alkylthio, C₁₋₆ haloalkylthio orNR¹³R¹⁴ where R¹³ and R¹⁴ are independently hydrogen, C₁₋₆ alkyl or C₁₋₆haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₂₋₆ alkylcarbonyl, phenylcarbonyl,(where the phenyl is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino), phenyl(C₁₋₃)alkyl (wherein the phenyl group maybe optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacentpositions on the phenyl ring may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen) or heteroaryl(C₁₋₃)alkyl (wherein the heteroaryl group maybe optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆alkylcarbonylamino, arylcarbonyl, or two adjacent positions on theheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen).

Even more preferably R¹ is C₁₋₆ alkyl, C₁₋₆ haloalkyl,heteroaryl(C₁₋₃)alkyl (wherein the heteroaryl group may be optionallysubstituted by halo, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl and where theheteroaryl group is a thiazole, pyridine, pyrimidine, pyrazine orpyridazine ring), heteroaryl (optionally substituted by halo, cyano,C₁₋₆ alkyl, C₁₋₆ haloalkyl and where the heteroaryl group is a pyridine,pyrimidine, 2,1,3-benzoxadiazole, pyrazine or pyridazine ring), C₁₋₆alkoxy, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₁₋₆ alkylamino, C₁₋₆alkyoxy(C₁₋₆)alkylamino or heteroaryl(C₁₋₃)alkylamino (wherein theheteroaryl group may be optionally substituted by halo, cyano, C₁₋₆alkyl, C₁₋₆ haloalkyl and where the heteroaryl group is a thiazole,pyridine, pyrimidine, pyrazine or pyridazine ring).

Most preferably R¹ is pyridyl (optionally substituted by halo, C₁₋₃alkyl or C₁₋₃ haloalkyl) especially halo-substituted pyridyl.

It is preferred that R² is hydrogen, hydroxy, C₁₋₆ alkyl or C₁₋₆haloalkyl.

More preferably R² is hydrogen, C₁₋₄ alkyl or C₁₋₄ haloalkyl.

Even more preferably R² is hydrogen or C₁₋₄ alkyl.

Yet more preferably R² is independently hydrogen or methyl.

Most preferably R² is hydrogen.

It is preferred that R³ is hydrogen, hydroxy, halogen, C₁₋₆ alkyl orC₁₋₆ haloalkyl.

More preferably R³ is hydrogen, hydroxy, halogen, C₁₋₄ alkyl or C₁₋₄haloalkyl.

Even more preferably R³ is hydrogen or C₁₋₄ alkyl.

Yet more preferably R³ is independently hydrogen or methyl.

Most preferably R³ is hydrogen.

R^(3a) is preferably hydrogen or R³ and R^(3a) together form a doublebond.

Preferably each R⁴ is independently halogen, cyano, C₁₋₈ alkyl, C₁₋₈haloalkyl, cyanoalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₃₋₇cycloalkyl(C₁₋₆)alkyl, C₅₋₆ cycloalkenyl(C₁₋₆)alkyl, C₃₋₆alkenyloxy(C₁₋₆)alkyl, C₃₋₆ alkynyloxy(C₁₋₆)alkyl, aryloxy(C₁₋₆)alkyl,C₁₋₆ carboxyalkyl, C₁₋₆ alkylcarbonyl(C₁₋₆)alkyl, C₂₋₆alkenylcarbonyl(C₁₋₆)alkyl, C₂₋₆ alkynylcarbonyl(C₁₋₆)-alkyl, C₁₋₆alkoxycarbonyl(C₁₋₆)alkyl, C₃₋₆ alkenyloxycarbonyl(C₁₋₆)alkyl, C₃₋₆alkynyloxycarbonyl(C₁₋₆)alkyl, aryloxycarbonyl(C₁₋₆)alkyl, C₁₋₆alkylthio(C₁₋₆)alkyl, C₁₋₆ alkylsulfinyl(C₁₋₆)alkyl, C₁₋₆alkylsulfonyl(C₁₋₆)alkyl, aminocarbonyl(C₁₋₆)alkyl, C₁₋₆alkylaminocarbonyl(C₁₋₆)alkyl, di(C₁₋₆)alkylaminocarbonyl(C₁₋₆)alkyl,phenyl(C₁₋₄)alkyl (wherein the phenyl group is optionally substituted byhalogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN,NO₂, aryl, heteroaryl, amino or dialkylamino), heteroaryl(C₁₋₄)alkyl(wherein the heteroaryl group is optionally substituted by halo, nitro,cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy),heterocyclyl(C₁₋₄alkyl (wherein the heterocyclyl group is optionallysubstituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy or C₁₋₆ haloalkoxy), C₂₋₆ alkenyl, aminocarbonyl(C₂₋₆)alkenyl,C₁₋₆ alkylaminocarbonyl(C₂₋₆)alkenyl,di(C₁₋₆)alkylaminocarbonyl(C₂₋₆)alkenyl, phenyl(C₂₋₄)-alkenyl, (whereinthe phenyl group is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino), C₂₋₆ alkynyl, trimethylsilyl(C₂₋₆)alkynyl,aminocarbonyl(C₂₋₆)alkynyl, C₁₋₆ alkylaminocarbonyl(C₂₋₆)alkynyl,di(C₁₋₆)alkylaminocarbonyl(C₂₋₆)alkynyl, C₁₋₆ alkoxycarbonyl, C₃₋₇cycloalkyl, C₃₋₇ halocycloalkyl, C₃₋₇ cyanocycloalkyl, C₁₋₃alkykC₃₋₇)-cycloalkyl, C₁₋₃ alkyl(C₃₋₇)halocycloalkyl,phenyl (optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino),heteroaryl (optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl,C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), heterocyclyl (whereinthe heterocyclyl group is optionally substituted by halo, nitro, cyano,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), or 2adjacent groups R⁴ together with the carbon atoms to which they areattached form a 4, 5, 6 or 7 membered carbocylic or heterocyclic ringwhich may be optionally substituted by halogen, C₁₋₈ alkoxy, C₁₋₆haloalkoxy, phenoxy (optionally substituted by halo, nitro, cyano, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), heteroaryloxy(optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), C₁₋₈ alkylthio or R¹⁹R²⁰Nwhere R¹⁹ and R²⁰ are, independently, hydrogen, C₁₋₈ alkyl, C₃₋₇cycloalkyl, C₃₋₆ alkenyl, C₃₋₆ alkynyl, C₂₋₆ haloalkyl, C₁₋₆alkoxycarbonyl or R¹⁹ and R²⁰ together with the N atom to which they areattached form a five, six or seven-membered heterocyclic ring which maycontain one or two further heteroatoms selected from O, N or S and whichmay be optionally substituted by one or two C₁₋₆ alkyl groups; n is 0,1, 2 or 3.

More preferably each R⁴ is independently halogen, cyano, C₁₋₈ alkyl,C₁₋₈ haloalkyl, C₁₋₈ cyanoalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₂₋₆ alkynyl,trimethylsilyl(C₂₋₆)alkynyl, C₁₋₆ alkoxycarbonyl, C₃₋₇ cycloalkyl, C₁₋₃alkyl(C₃₋₇) cycloalkyl, phenyl (optionally substituted by halogen, C₁₋₄alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl,heteroaryl, amino or dialkylamino), heterocyclyl (optionally substitutedby halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆haloalkoxy), C₁₋₈ alkoxy, C₁₋₆ haloalkoxy, phenoxy (optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino),heteroaryloxy (optionally substituted by halo, nitro, cyano, C₁₋₃ alkyl,C₁₋₃ haloalkyl, C₁₋₃ alkoxy or C₁₋₃ haloalkoxy), di(C₁₋₈)alkylamino, or2 adjacent groups R⁴ together with the carbon atoms to which they areattached form a 4, 5, 6 or 7 membered carbocylic or heterocyclic ringwhich may be optionally substituted by halogen; n is 0, 1, 2 or 3.

Even more preferably each R⁴ is independently halogen, cyano, C₁₋₈alkyl, C₁₋₈ haloalkyl, C₁₋₈ cyanoalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₂₋₆alkynyl, heterocyclyl (optionally substituted by C₁₋₆ alkyl), C₁₋₈alkoxy, C₁₋₆ haloalkoxy, phenoxy (optionally substituted by halo, cyano,C₁₋₃ alkyl or C₁₋₃ haloalkyl), heteroaryloxy (optionally substituted byhalo, cyano, C₁₋₃ alkyl or C₁₋₃ haloalkyl), di(C₁₋₈)alkylamino or 2adjacent groups R⁴ together with the carbon atoms to which they areattached form a 4, 5, 6 or 7 membered carbocylic or heterocyclic ringwhich may be optionally substituted by halogen; n is 0, 1, 2 or 3.

Yet more preferably each R⁴ is independently fluoro, chloro, bromo,cyano, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ cyanoalkyl or C₁₋₃alkoxy(C₁₋₃)alkyl; n is 0, 1, 2 or 3, preferably 0, 1 or 2.

Most preferably each R⁴ is independently fluoro, chloro, bromo, C₁₋₄alkyl or C₁₋₄ haloalkyl; n is 1, 2 or 3, preferably 1 or 2.

Preferably R⁸ is C₁₋₁₀ alkyl, C₁₋₁₀ haloalkyl, aryl(C₁₋₆)alkyl (whereinthe aryl group is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino), heteroaryl(C₁₋₆)alkyl (wherein the heteroarylgroup is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy,C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino), arylcarbonyl-(C₁₋₆)alkyl (wherein the aryl group may beoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino and the alkyl group may be optionally substituted by aryl),C₂₋₈ alkenyl, C₂₋₈ haloalkenyl, aryl(C₂₋₆)-alkenyl (wherein the arylgroup is optionally substituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino, C₁₋₆ alkoxycarbonyl, or two adjacent substituents cancyclise to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring),heteroaryl(C₂₋₆)-alkenyl (wherein the heteroaryl group is optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino, C₁₋₆alkoxycarbonyl, or two adjacent substituents can cyclise to form a 5, 6or 7 membered carbocyclic or heterocyclic ring), C₂₋₆ alkynyl,phenyl(C₂₋₆)alkynyl (wherein the phenyl group is optionally substitutedby halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy,CN, NO₂, aryl, heteroaryl, amino or dialkylamino), C₃₋₇ cycloalkyl, C₁₋₆alkoxycarbonyl, C₁₋₆ alkylcarbonyl, C₁₋₆ haloalkylcarbonyl oraryl(C₂₋₆)alkenylcarbonyl (wherein the aryl group may be optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino), or—C(R⁵¹)(R⁵²)—[CR⁵³═CR⁵⁴]z-R⁵⁵ where z is 1 or 2, R⁵¹ and R⁵² are eachindependently H, halo or C₁₋₂ alkyl, R⁵³ and R⁵⁴ are each independentlyH, halogen, C₁₋₄ alkyl or C₁₋₄ haloalkyl and R⁵⁵ is optionallysubstituted aryl or optionally substituted heteroaryl.

More preferably R⁸ is phenyl(C₁₋₄alkyl (wherein the phenyl group isoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino), heteroaryl(C₁₋₆)alkyl (wherein the heteroaryl group isoptionally substituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl,C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino),phenyl(C₂₋₆)alkenyl (wherein the phenyl group is optionally substitutedby halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy,CN, NO₂, aryl, heteroaryl, amino or dialkylamino),heteroaryl(C₂₋₆)alkenyl (wherein the heteroaryl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino) orphenyl(C₂₋₆)alkynyl (wherein the phenyl group is optionally substitutedby halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy,CN, NO₂, aryl, heteroaryl, amino or dialkylamino, or—C(R⁵¹)(R⁵²)—[CR⁵³═CR⁵⁴]z-R⁵⁵ where z is 1 or 2, R⁵¹ and R⁵² are eachindependently H, halo or C₁₋₂ alkyl, R⁵³ and R⁵⁴ are each independentlyH, halogen, C₁₋₄ alkyl or C₁₋₄ haloalkyl and R⁵⁵ is optionallysubstituted aryl or optionally substituted heteroaryl.

Most preferably R⁸ is —C(R⁵¹)(R⁵²)—[CR⁵³═CR⁵⁴]z-R⁵⁵ where z is 1 or 2,preferably 1, R⁵¹ and R⁵² are each independently H or C₁₋₂ alkyl, R⁵³and R⁵⁴ are each independently H, halogen, C₁₋₄ alkyl or C₁₋₄ haloalkyland R⁵⁵ is phenyl substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino or heteroaryl substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino.

R⁵¹ and R⁵² are preferably hydrogen.

R⁵³ and R⁵⁴ are preferably hydrogen or halogen, especially hydrogen.

R⁵⁵ is preferably phenyl substituted with one to three substituentsselected from halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino.

Preferably each Ra is independently halo, cyano, C₁₋₃ alkyl, hydroxy ortwo Ra groups together with the carbon atom to which they are attachedform ═O, ═S, ═NRb, ═CRcRd where Rb, Rc and Rd are independently H oroptionally substituted alkyl, and p is 0, 1 or 2.

More preferably each Ra is independently fluoro, methyl, hydroxy or twoRa groups together with the carbon atom to which they are attached forma carbonyl group and p is 0, 1 or 2.

Most preferably p is 0.

It is preferred that that ring

is a 6-membered aromatic ring or is 5 or 6 membered heteroaromatic ringwherein the ring members other than Z and Z′ are each independently CH,S, N, NR⁴, O, or CR⁴ provided that there are no more than one O or Satoms present in the ring.

More preferably the ring

is a benzene, pyridine, pyrimidine, pyrazine, pyridazine, triazine,pyrrole, imidazole, quinoline, isoquinoline, thiophene, pyrazole,oxazole, thiazole, isoxazole, isothiazole, [1,2,3]triazole,[1,2,3]oxadiazole or [1,2,3]thiadiazole.

Most preferably the ring

is a benzene, pyridine, pyrimidine, pyrazine, thiophene or pyrazolering, especially a benzene ring.

Certain compounds of formula (I) are novel and as such form a furtheraspect of the invention. One group of novel compounds are compounds offormula I′

wherein R¹, R², R³, R^(3a), R⁴Ra, T, Y, n and p are as defined inrelation to formula I and R⁸ is —C(R⁵¹)(R⁵²)—[CR⁵³═CR⁵⁴]z-R⁵⁵ where z is1 or 2, preferably 1, R⁵¹ and R⁵² are each independently H or C₁₋₂alkyl, R⁵³ and R⁵⁴ are each independently H, halogen, C₁₋₄ alkyl or C₁₋₄haloalkyl and R⁵⁵ is phenyl substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino or heteroaryl substituted by halogen, C₁₋₄ alkyl,C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino or salts or N-oxides thereof.

The compounds in Tables I to XCV below illustrate the compounds of theinvention.

Table I provides 1127 compounds of formula Ia

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

TABLE 1 Compound No R⁸ R^(4a) R^(4b) R^(4c) R^(4d) I-1 4-chlorobenzyl HH H H I-2 Cinnamyl H H H H I-3 4-chlorocinnamyl H H H H I-44-fluorocinnamyl H H H H I-5 4-bromocinnamyl H H H H I-64-trifluoromethylcinnamyl H H H H I-7 4-trifluoromethoxycinnamyl H H H HI-8 4-pentafluoroethoxycinnamyl H H H H I-9 4-methoxycinnamyl H H H HI-10 4-ethoxycinnamyl H H H H I-11 4-cyanocinnamyl H H H H I-123-(6-chloro-pyridin-3-yl)-allyl H H H H I-133-(4-chlorophenyl)-but-2-enyl H H H H I-143-(4-chlorophenyl)-3-fluoro-allyl H H H H I-153-chloro-4-fluoro-cinnamyl H H H H I-16 3,5-dichloro-cinnamyl H H H HI-17 5-phenyl-penta-2,4-dienyl H H H H I-18 4-isopropyloxycarbonylamino-H H H H cinnamyl I-19 3-naphthalen-2-yl-allyl H H H H I-203-(5-trifluoromethyl-pyridin-2- H H H H yl)-allyl I-213-(5-chloro-pyridin-2-yl)-allyl H H H H I-22 3-pyridin-4-yl-allyl H H HH I-23 3-(2-Chloro-pyridin-4-yl)-allyl H H H H I-24 4-chlorobenzyl H F HH I-25 Cinnamyl H F H H I-26 4-chlorocinnamyl H F H H I-274-fluorocinnamyl H F H H I-28 4-bromocinnamyl H F H H I-294-trifluoromethylcinnamyl H F H H I-30 4-trifluoromethoxycinnamyl H F HH I-31 4-pentafluoroethoxycinnamyl H F H H I-32 4-methoxycinnamyl H F HH I-33 4-ethoxycinnamyl H F H H I-34 4-cyanocinnamyl H F H H I-353-(6-chloro-pyridin-3-yl)-allyl H F H H I-363-(4-chlorophenyl)-but-2-enyl H F H H I-37 3-(4-chlorophenyl)-3-fluoro-H F H H allyl I-38 3-chloro-4-fluoro-cinnamyl H F H H I-393,5-dichloro-cinnamyl H F H H I-40 5-phenyl-penta-2,4-dienyl H F H HI-41 4-isopropyloxycarbonylamino- H F H H cinnamyl I-423-naphthalen-2-yl-allyl H F H H I-43 3-(5-trifluoromethyl-pyridin-2-yl)-H F H H allyl I-44 3-(5-chloro-pyridin-2-yl)-allyl H F H H I-453-pyridin-4-yl-allyl H F H H I-46 3-(2-Chloro-pyridin-4-yl)-allyl H F HH I-47 4-chlorobenzyl H Cl H H I-48 Cinnamyl H Cl H H I-494-chlorocinnamyl H Cl H H I-50 4-fluorocinnamyl H Cl H H I-514-bromocinnamyl H Cl H H I-52 4-trifluoromethylcinnamyl H Cl H H I-534-trifluoromethoxycinnamyl H Cl H H I-54 4-pentafluoroethoxycinnamyl HCl H H I-55 4-methoxycinnamyl H Cl H H I-56 4-ethoxycinnamyl H Cl H HI-57 4-cyanocinnamyl H Cl H H I-58 3-(6-chloro-pyridin-3-yl)-allyl H ClH H I-59 3-(4-chlorophenyl)-but-2-enyl H Cl H H I-603-(4-chlorophenyl)-3-fluoro-allyl H Cl H H I-613-chloro-4-fluoro-cinnamyl H Cl H H I-62 3,5-dichloro-cinnamyl H Cl H HI-63 5-phenyl-penta-2,4-dienyl H Cl H H I-644-isopropyloxycarbonylamino- H Cl H H cinnamyl I-653-naphthalen-2-yl-allyl H Cl H H I-66 3-(5-trifluoromethyl-pyridin-2- HCl H H yl)-allyl I-67 3-(5-chloro-pyridin-2-yl)-allyl H Cl H H I-683-pyridin-4-yl-allyl H Cl H H I-69 3-(2-Chloro-pyridin-4-yl)-allyl H ClH H I-70 4-chlorobenzyl H H F H I-71 Cinnamyl H H F H I-724-chlorocinnamyl H H F H I-73 4-fluorocinnamyl H H F H I-744-bromocinnamyl H H F H I-75 4-trifluoromethylcinnamyl H H F H I-764-trifluoromethoxycinnamyl H H F H I-77 4-pentafluoroethoxycinnamyl H HF H I-78 4-methoxycinnamyl H H F H I-79 4-ethoxycinnamyl H H F H I-804-cyanocinnamyl H H F H I-81 3-(6-chloro-pyridin-3-yl)-allyl H H F HI-82 3-(4-chlorophenyl)-but-2-enyl H H F H I-833-(4-chlorophenyl)-3-fluoro- H H F H allyl I-843-chloro-4-fluoro-cinnamyl H H F H I-85 3,5-dichloro-cinnamyl H H F HI-86 5-phenyl-penta-2,4-dienyl H H F H I-87 4-isopropyloxycarbonylamino-H H F H cinnamyl I-88 3-naphthalen-2-yl-allyl H H F H I-893-(5-trifluoromethyl-pyridin-2- H H F H yl)-allyl I-903-(5-chloro-pyridin-2-yl)-allyl H H F H I-91 3-pyridin-4-yl-allyl H H FH I-92 3-(2-Chloro-pyridin-4-yl)-allyl H H F H I-93 4-chlorobenzyl H HCl H I-94 Cinnamyl H H Cl H I-95 4-chlorocinnamyl H H Cl H I-964-fluorocinnamyl H H Cl H I-97 4-bromocinnamyl H H Cl H I-984-trifluoromethylcinnamyl H H Cl H I-99 4-trifluoromethoxycinnamyl H HCl H I-100 4-pentafluoroethoxycinnamyl H H Cl H I-101 4-methoxycinnamylH H Cl H I-102 4-ethoxycinnamyl H H Cl H I-103 4-cyanocinnamyl H H Cl HI-104 3-(6-chloro-pyridin-3-yl)-allyl H H Cl H I-1053-(4-chlorophenyl)-but-2-enyl H H Cl H I-1063-(4-chlorophenyl)-3-fluoro- H H Cl H allyl I-1073-chloro-4-fluoro-cinnamyl H H Cl H I-108 3,5-dichloro-cinnamyl H H Cl HI-109 5-phenyl-penta-2,4-dienyl H H Cl H I-1104-isopropyloxycarbonylamino- H H Cl H cinnamyl I-1113-naphthalen-2-yl-allyl H H Cl H I-112 3-(5-trifluoromethyl-pyridin-2- HH Cl H yl)-allyl I-113 3-(5-chloro-pyridin-2-yl)-allyl H H Cl H I-1143-pyridin-4-yl-allyl H H Cl H I-115 3-(2-Chloro-pyridin-4-yl)-allyl H HCl H I-116 4-chlorobenzyl Cl Cl H H I-117 Cinnamyl Cl Cl H H I-1184-chlorocinnamyl Cl Cl H H I-119 4-fluorocinnamyl Cl Cl H H I-1204-bromocinnamyl Cl Cl H H I-121 4-trifluoromethylcinnamyl Cl Cl H HI-122 4-trifluoromethoxycinnamyl Cl Cl H H I-1234-pentafluoroethoxycinnamyl Cl Cl H H I-124 4-methoxycinnamyl Cl Cl H HI-125 4-ethoxycinnamyl Cl Cl H H I-126 4-cyanocinnamyl Cl Cl H H I-1273-(6-chloro-pyridin-3-yl)-allyl Cl Cl H H I-1283-(4-chlorophenyl)-but-2-enyl Cl Cl H H I-1293-(4-chlorophenyl)-3-fluoro- Cl Cl H H allyl I-1303-chloro-4-fluoro-cinnamyl Cl Cl H H I-131 3,5-dichloro-cinnamyl Cl Cl HH I-132 5-phenyl-penta-2,4-dienyl Cl Cl H H I-1334-isopropyloxycarbonylamino- Cl Cl H H cinnamyl I-1343-naphthalen-2-yl-allyl Cl Cl H H I-135 3-(5-trifluoromethyl-pyridin-2-Cl Cl H H yl)-allyl I-136 3-(5-chloro-pyridin-2-yl)-allyl Cl Cl H HI-137 3-pyridin-4-yl-allyl Cl Cl H H I-1383-(2-Chloro-pyridin-4-yl)-allyl Cl Cl H H I-139 4-chlorobenzyl F F H HI-140 Cinnamyl F F H H I-141 4-chlorocinnamyl F F H H I-1424-fluorocinnamyl F F H H I-143 4-bromocinnamyl F F H H I-1444-trifluoromethylcinnamyl F F H H I-145 4-trifluoromethoxycinnamyl F F HH I-146 4-pentafluoroethoxycinnamyl F F H H I-147 4-methoxycinnamyl F FH H I-148 4-ethoxycinnamyl F F H H I-149 4-cyanocinnamyl F F H H I-1503-(6-chloro-pyridin-3-yl)-allyl F F H H I-1513-(4-chlorophenyl)-but-2-enyl F F H H I-152 3-(4-chlorophenyl)-3-fluoro-F F H H allyl I-153 3-chloro-4-fluoro-cinnamyl F F H H I-1543,5-dichloro-cinnamyl F F H H I-155 5-phenyl-penta-2,4-dienyl F F H HI-156 4-isopropyloxycarbonylamino- F F H H cinnamyl I-1573-naphthalen-2-yl-allyl F F H H I-158 3-(5-trifluoromethyl-pyridin-2- FF H H yl)-allyl I-159 3-(5-chloro-pyridin-2-yl)-allyl F F H H I-1603-pyridin-4-yl-allyl F F H H I-161 3-(2-Chloro-pyridin-4-yl)-allyl F F HH I-162 4-chlorobenzyl F H F H I-163 Cinnamyl F H F H I-1644-chlorocinnamyl F H F H I-165 4-fluorocinnamyl F H F H I-1664-bromocinnamyl F H F H I-167 4-trifluoromethylcinnamyl F H F H I-1684-trifluoromethoxycinnamyl F H F H I-169 4-pentafluoroethoxycinnamyl F HF H I-170 4-methoxycinnamyl F H F H I-171 4-ethoxycinnamyl F H F H I-1724-cyanocinnamyl F H F H I-173 3-(6-chloro-pyridin-3-yl)-allyl F H F HI-174 3-(4-chlorophenyl)-but-2-enyl F H F H I-1753-(4-chlorophenyl)-3-fluoro- F H F H allyl I-1763-chloro-4-fluoro-cinnamyl F H F H I-177 3,5-dichloro-cinnamyl F H F HI-178 5-phenyl-penta-2,4-dienyl F H F H I-1794-isopropyloxycarbonylamino- F H F H cinnamyl I-1803-naphthalen-2-yl-allyl F H F H I-181 3-(5-trifluoromethyl-pyridin-2- FH F H yl)-allyl I-182 3-(5-chloro-pyridin-2-yl)-allyl F H F H I-1833-pyridin-4-yl-allyl F H F H I-184 3-(2-Chloro-pyridin-4-yl)-allyl F H FH I-185 4-chlorobenzyl F H H F I-186 Cinnamyl F H H F I-1874-chlorocinnamyl F H H F I-188 4-fluorocinnamyl F H H F I-1894-bromocinnamyl F H H F I-190 4-trifluoromethylcinnamyl F H H F I-1914-trifluoromethoxycinnamyl F H H F I-192 4-pentafluoroethoxycinnamyl F HH F I-193 4-methoxycinnamyl F H H F I-194 4-ethoxycinnamyl F H H F I-1954-cyanocinnamyl F H H F I-196 3-(6-chloro-pyridin-3-yl)-allyl F H H FI-197 3-(4-chlorophenyl)-but-2-enyl F H H F I-1983-(4-chlorophenyl)-3-fluoro- F H H F allyl I-1993-chloro-4-fluoro-cinnamyl F H H F I-200 3,5-dichloro-cinnamyl F H H FI-201 5-phenyl-penta-2,4-dienyl F H H F I-2024-isopropyloxycarbonylamino- F H H F cinnamyl I-2033-naphthalen-2-yl-allyl F H H F I-204 3-(5-trifluoromethyl-pyridin-2- FH H F yl)-allyl I-205 3-(5-chloro-pyridin-2-yl)-allyl F H H F I-2063-pyridin-4-yl-allyl F H H F I-207 3-(2-Chloro-pyridin-4-yl)-allyl F H HF I-208 4-chlorobenzyl Cl H Cl H I-209 Cinnamyl Cl H Cl H I-2104-chlorocinnamyl Cl H Cl H I-211 4-fluorocinnamyl Cl H Cl H I-2124-bromocinnamyl Cl H Cl H I-213 4-trifluoromethylcinnamyl Cl H Cl HI-214 4-trifluoromethoxycinnamyl Cl H Cl H I-2154-pentafluoroethoxycinnamyl Cl H Cl H I-216 4-methoxycinnamyl Cl H Cl HI-217 4-ethoxycinnamyl Cl H Cl H I-218 4-cyanocinnamyl Cl H Cl H I-2193-(6-chloro-pyridin-3-yl)-allyl Cl H Cl H I-2203-(4-chlorophenyl)-but-2-enyl Cl H Cl H I-2213-(4-chlorophenyl)-3-fluoro- Cl H Cl H allyl I-2223-chloro-4-fluoro-cinnamyl Cl H Cl H I-223 3,5-dichloro-cinnamyl Cl H ClH I-224 5-phenyl-penta-2,4-dienyl Cl H Cl H I-2254-isopropyloxycarbonylamino- Cl H Cl H cinnamyl I-2263-naphthalen-2-yl-allyl Cl H Cl H I-227 3-(5-trifluoromethyl-pyridin-2-Cl H Cl H yl)-allyl I-228 3-(5-chloro-pyridin-2-yl)-allyl Cl H Cl HI-229 3-pyridin-4-yl-allyl Cl H Cl H I-2303-(2-Chloro-pyridin-4-yl)-allyl Cl H Cl H I-231 4-chlorobenzyl Cl H H ClI-232 Cinnamyl Cl H H Cl I-233 4-chlorocinnamyl Cl H H Cl I-2344-fluorocinnamyl Cl H H Cl I-235 4-bromocinnamyl Cl H H Cl I-2364-trifluoromethylcinnamyl Cl H H Cl I-237 4-trifluoromethoxycinnamyl ClH H Cl I-238 4-pentafluoroethoxycinnamyl Cl H H Cl I-2394-methoxycinnamyl Cl H H Cl I-240 4-ethoxycinnamyl Cl H H Cl I-2414-cyanocinnamyl Cl H H Cl I-242 3-(6-chloro-pyridin-3-yl)-allyl Cl H HCl I-243 3-(4-chlorophenyl)-but-2-enyl Cl H H Cl I-2443-(4-chlorophenyl)-3-fluoro- Cl H H Cl allyl I-2453-chloro-4-fluoro-cinnamyl Cl H H Cl I-246 3,5-dichloro-cinnamyl Cl H HCl I-247 5-phenyl-penta-2,4-dienyl Cl H H Cl I-2484-isopropyloxycarbonylamino- Cl H H Cl cinnamyl I-2493-naphthalen-2-yl-allyl Cl H H Cl I-250 3-(5-trifluoromethyl-pyridin-2-Cl H H Cl yl)-allyl I-251 3-(5-chloro-pyridin-2-yl)-allyl Cl H H ClI-252 3-pyridin-4-yl-allyl Cl H H Cl I-2533-(2-Chloro-pyridin-4-yl)-allyl Cl H H Cl I-254 4-chlorobenzyl F Cl H HI-255 Cinnamyl F Cl H H I-256 4-chlorocinnamyl F Cl H H I-2574-fluorocinnamyl F Cl H H I-258 4-bromocinnamyl F Cl H H I-2594-trifluoromethylcinnamyl F Cl H H I-260 4-trifluoromethoxycinnamyl F ClH H I-261 4-pentafluoroethoxycinnamyl F Cl H H I-262 4-methoxycinnamyl FCl H H I-263 4-ethoxycinnamyl F Cl H H I-264 4-cyanocinnamyl F Cl H HI-265 3-(6-chloro-pyridin-3-yl)-allyl F Cl H H I-2663-(4-chlorophenyl)-but-2-enyl F Cl H H I-2673-(4-chlorophenyl)-3-fluoro- F Cl H H allyl I-2683-chloro-4-fluoro-cinnamyl F Cl H H I-269 3,5-dichloro-cinnamyl F Cl H HI-270 5-phenyl-penta-2,4-dienyl F Cl H H I-2714-isopropyloxycarbonylamino- F Cl H H cinnamyl I-2723-naphthalen-2-yl-allyl F Cl H H I-273 3-(5-trifluoromethyl-pyridin-2- FCl H H yl)-allyl I-274 3-(5-chloro-pyridin-2-yl)-allyl F Cl H H I-2753-pyridin-4-yl-allyl F Cl H H I-276 3-(2-Chloro-pyridin-4-yl)-allyl F ClH H I-277 4-chlorobenzyl F H Cl H I-278 Cinnamyl F H Cl H I-2794-chlorocinnamyl F H Cl H I-280 4-fluorocinnamyl F H Cl H I-2814-bromocinnamyl F H Cl H I-282 4-trifluoromethylcinnamyl F H Cl H I-2834-trifluoromethoxycinnamyl F H Cl H I-284 4-pentafluoroethoxycinnamyl FH Cl H I-285 4-methoxycinnamyl F H Cl H I-286 4-ethoxycinnamyl F H Cl HI-287 4-cyanocinnamyl F H Cl H I-288 3-(6-chloro-pyridin-3-yl)-allyl F HCl H I-289 3-(4-chlorophenyl)-but-2-enyl F H Cl H I-2903-(4-chlorophenyl)-3-fluoro- F H Cl H allyl I-2913-chloro-4-fluoro-cinnamyl F H Cl H I-292 3,5-dichloro-cinnamyl F H Cl HI-293 5-phenyl-penta-2,4-dienyl F H Cl H I-2944-isopropyloxycarbonylamino- F H Cl H cinnamyl I-2953-naphthalen-2-yl-allyl F H Cl H I-296 3-(5-trifluoromethyl-pyridin-2- FH Cl H yl)-allyl I-297 3-(5-chloro-pyridin-2-yl)-allyl F H Cl H I-2983-pyridin-4-yl-allyl F H Cl H I-299 3-(2-Chloro-pyridin-4-yl)-allyl F HCl H I-300 4-chlorobenzyl F H H Cl I-301 Cinnamyl F H H Cl I-3024-chlorocinnamyl F H H Cl I-303 4-fluorocinnamyl F H H Cl I-3044-bromocinnamyl F H H Cl I-305 4-trifluoromethylcinnamyl F H H Cl I-3064-trifluoromethoxycinnamyl F H H Cl I-307 4-pentafluoroethoxycinnamyl FH H Cl I-308 4-methoxycinnamyl F H H Cl I-309 4-ethoxycinnamyl F H H ClI-310 4-cyanocinnamyl F H H Cl I-311 3-(6-chloro-pyridin-3-yl)-allyl F HH Cl I-312 3-(4-chlorophenyl)-but-2-enyl F H H Cl I-3133-(4-chlorophenyl)-3-fluoro- F H H Cl allyl I-3143-chloro-4-fluoro-cinnamyl F H H Cl I-315 3,5-dichloro-cinnamyl F H H ClI-316 5-phenyl-penta-2,4-dienyl F H H Cl I-3174-isopropyloxycarbonylamino- F H H Cl cinnamyl I-3183-naphthalen-2-yl-allyl F H H Cl I-319 3-(5-trifluoromethyl-pyridin-2- FH H Cl yl)-allyl I-320 3-(5-chloro-pyridin-2-yl)-allyl F H H Cl I-3213-pyridin-4-yl-allyl F H H Cl I-322 3-(2-Chloro-pyridin-4-yl)-allyl F HH Cl I-323 4-chlorobenzyl Cl F H H I-324 Cinnamyl Cl F H H I-3254-chlorocinnamyl Cl F H H I-326 4-fluorocinnamyl Cl F H H I-3274-bromocinnamyl Cl F H H I-328 4-trifluoromethylcinnamyl Cl F H H I-3294-trifluoromethoxycinnamyl Cl F H H I-330 4-pentafluoroethoxycinnamyl ClF H H I-331 4-methoxycinnamyl Cl F H H I-332 4-ethoxycinnamyl Cl F H HI-333 4-cyanocinnamyl Cl F H H I-334 3-(6-chloro-pyridin-3-yl)-allyl ClF H H I-335 3-(4-chlorophenyl)-but-2-enyl Cl F H H I-3363-(4-chlorophenyl)-3-fluoro- Cl F H H allyl I-3373-chloro-4-fluoro-cinnamyl Cl F H H I-338 3,5-dichloro-cinnamyl Cl F H HI-339 5-phenyl-penta-2,4-dienyl Cl F H H I-3404-isopropyloxycarbonylamino- Cl F H H cinnamyl I-3413-naphthalen-2-yl-allyl Cl F H H I-342 3-(5-trifluoromethyl-pyridin-2-Cl F H H yl)-allyl I-343 3-(5-chloro-pyridin-2-yl)-allyl Cl F H H I-3443-pyridin-4-yl-allyl Cl F H H I-345 3-(2-Chloro-pyridin-4-yl)-allyl Cl FH H I-346 4-chlorobenzyl H F Cl H I-347 Cinnamyl H F Cl H I-3484-chlorocinnamyl H F Cl H I-349 4-fluorocinnamyl H F Cl H I-3504-bromocinnamyl H F Cl H I-351 4-trifluoromethylcinnamyl H F Cl H I-3524-trifluoromethoxycinnamyl H F Cl H I-353 4-pentafluoroethoxycinnamyl HF Cl H I-354 4-methoxycinnamyl H F Cl H I-355 4-ethoxycinnamyl H F Cl HI-356 4-cyanocinnamyl H F Cl H I-357 3-(6-chloro-pyridin-3-yl)-allyl H FCl H I-358 3-(4-chlorophenyl)-but-2-enyl H F Cl H I-3593-(4-chlorophenyl)-3-fluoro- H F Cl H allyl I-3603-chloro-4-fluoro-cinnamyl H F Cl H I-361 3,5-dichloro-cinnamyl H F Cl HI-362 5-phenyl-penta-2,4-dienyl H F Cl H I-3634-isopropyloxycarbonylamino- H F Cl H cinnamyl I-3643-naphthalen-2-yl-allyl H F Cl H I-365 3-(5-trifluoromethyl-pyridin-2- HF Cl H yl)-allyl I-366 3-(5-chloro-pyridin-2-yl)-allyl H F Cl H I-3673-pyridin-4-yl-allyl H F Cl H I-368 3-(2-Chloro-pyridin-4-yl)-allyl H FCl H I-369 4-chlorobenzyl H F H Cl I-370 Cinnamyl H F H Cl I-3714-chlorocinnamyl H F H Cl I-372 4-fluorocinnamyl H F H Cl I-3734-bromocinnamyl H F H Cl I-374 4-trifluoromethylcinnamyl H F H Cl I-3754-trifluoromethoxycinnamyl H F H Cl I-376 4-pentafluoroethoxycinnamyl HF H Cl I-377 4-methoxycinnamyl H F H Cl I-378 4-ethoxycinnamyl H F H ClI-379 4-cyanocinnamyl H F H Cl I-380 3-(6-chloro-pyridin-3-yl)-allyl H FH Cl I-381 3-(4-chlorophenyl)-but-2-enyl H F H Cl I-3823-(4-chlorophenyl)-3-fluoro- H F H Cl allyl I-3833-chloro-4-fluoro-cinnamyl H F H Cl I-384 3,5-dichloro-cinnamyl H F H ClI-385 5-phenyl-penta-2,4-dienyl H F H Cl I-3864-isopropyloxycarbonylamino- H F H Cl cinnamyl I-3873-naphthalen-2-yl-allyl H F H Cl I-388 3-(5-trifluoromethyl-pyridin-2- HF H Cl yl)-allyl I-389 3-(5-chloro-pyridin-2-yl)-allyl H F H Cl I-3903-pyridin-4-yl-allyl H F H Cl I-391 3-(2-Chloro-pyridin-4-yl)-allyl H FH Cl I-392 4-chlorobenzyl Cl H F H I-393 Cinnamyl Cl H F H I-3944-chlorocinnamyl Cl H F H I-395 4-fluorocinnamyl Cl H F H I-3964-bromocinnamyl Cl H F H I-397 4-trifluoromethylcinnamyl Cl H F H I-3984-trifluoromethoxycinnamyl Cl H F H I-399 4-pentafluoroethoxycinnamyl ClH F H I-400 4-methoxycinnamyl Cl H F H I-401 4-ethoxycinnamyl Cl H F HI-402 4-cyanocinnamyl Cl H F H I-403 3-(6-chloro-pyridin-3-yl)-allyl ClH F H I-404 3-(4-chlorophenyl)-but-2-enyl Cl H F H I-4053-(4-chlorophenyl)-3-fluoro- Cl H F H allyl I-4063-chloro-4-fluoro-cinnamyl Cl H F H I-407 3,5-dichloro-cinnamyl Cl H F HI-408 5-phenyl-penta-2,4-dienyl Cl H F H I-4094-isopropyloxycarbonylamino- Cl H F H cinnamyl I-4103-naphthalen-2-yl-allyl Cl H F H I-411 3-(5-trifluoromethyl-pyridin-2-Cl H F H yl)-allyl I-412 3-(5-chloro-pyridin-2-yl)-allyl Cl H F H I-4133-pyridin-4-yl-allyl Cl H F H I-414 3-(2-Chloro-pyridin-4-yl)-allyl Cl HF H I-415 4-chlorobenzyl H Cl F H I-416 Cinnamyl H Cl F H I-4174-chlorocinnamyl H Cl F H I-418 4-fluorocinnamyl H Cl F H I-4194-bromocinnamyl H Cl F H I-420 4-trifluoromethylcinnamyl H Cl F H I-4214-trifluoromethoxycinnamyl H Cl F H I-422 4-pentafluoroethoxycinnamyl HCl F H I-423 4-methoxycinnamyl H Cl F H I-424 4-ethoxycinnamyl H Cl F HI-425 4-cyanocinnamyl H Cl F H I-426 3-(6-chloro-pyridin-3-yl)-allyl HCl F H I-427 3-(4-chlorophenyl)-but-2-enyl H Cl F H I-4283-(4-chlorophenyl)-3-fluoro- H Cl F H allyl I-4293-chloro-4-fluoro-cinnamyl H Cl F H I-430 3,5-dichloro-cinnamyl H Cl F HI-431 5-phenyl-penta-2,4-dienyl H Cl F H I-4324-isopropyloxycarbonylamino- H Cl F H cinnamyl I-4333-naphthalen-2-yl-allyl H Cl F H I-434 3-(5-trifluoromethyl-pyridin-2- HCl F H yl)-allyl I-435 3-(5-chloro-pyridin-2-yl)-allyl H Cl F H I-4363-pyridin-4-yl-allyl H Cl F H I-437 3-(2-Chloro-pyridin-4-yl)-allyl H ClF H I-438 4-chlorobenzyl H H F Cl I-439 Cinnamyl H H F Cl I-4404-chlorocinnamyl H H F Cl I-441 4-fluorocinnamyl H H F Cl I-4424-bromocinnamyl H H F Cl I-443 4-trifluoromethylcinnamyl H H F Cl I-4444-trifluoromethoxycinnamyl H H F Cl I-445 4-pentafluoroethoxycinnamyl HH F Cl I-446 4-methoxycinnamyl H H F Cl I-447 4-ethoxycinnamyl H H F ClI-448 4-cyanocinnamyl H H F Cl I-449 3-(6-chloro-pyridin-3-yl)-allyl H HF Cl I-450 3-(4-chlorophenyl)-but-2-enyl H H F Cl I-4513-(4-chlorophenyl)-3-fluoro- H H F Cl allyl I-4523-chloro-4-fluoro-cinnamyl H H F Cl I-453 3,5-dichloro-cinnamyl H H F ClI-454 5-phenyl-penta-2,4-dienyl H H F Cl I-4554-isopropyloxycarbonylamino- H H F Cl cinnamyl I-4563-naphthalen-2-yl-allyl H H F Cl I-457 3-(5-trifluoromethyl-pyridin-2- HH F Cl yl)-allyl I-458 3-(5-chloro-pyridin-2-yl)-allyl H H F Cl I-4593-pyridin-4-yl-allyl H H F Cl I-460 3-(2-Chloro-pyridin-4-yl)-allyl H HF Cl I-461 4-chlorobenzyl Cl H H F I-462 Cinnamyl Cl H H F I-4634-chlorocinnamyl Cl H H F I-464 4-fluorocinnamyl Cl H H F I-4654-bromocinnamyl Cl H H F I-466 4-trifluoromethylcinnamyl Cl H H F I-4674-trifluoromethoxycinnamyl Cl H H F I-468 4-pentafluoroethoxycinnamyl ClH H F I-469 4-methoxycinnamyl Cl H H F I-470 4-ethoxycinnamyl Cl H H FI-471 4-cyanocinnamyl Cl H H F I-472 3-(6-chloro-pyridin-3-yl)-allyl ClH H F I-473 3-(4-chlorophenyl)-but-2-enyl Cl H H F I-4743-(4-chlorophenyl)-3-fluoro- Cl H H F allyl I-4753-chloro-4-fluoro-cinnamyl Cl H H F I-476 3,5-dichloro-cinnamyl Cl H H FI-477 5-phenyl-penta-2,4-dienyl Cl H H F I-4784-isopropyloxycarbonylamino- Cl H H F cinnamyl I-4793-naphthalen-2-yl-allyl Cl H H F I-480 3-(5-trifluoromethyl-pyridin-2-Cl H H F yl)-allyl I-481 3-(5-chloro-pyridin-2-yl)-allyl Cl H H F I-4823-pyridin-4-yl-allyl Cl H H F I-483 3-(2-Chloro-pyridin-4-yl)-allyl Cl HH F I-484 4-chlorobenzyl H Cl H F I-485 Cinnamyl H Cl H F I-4864-chlorocinnamyl H Cl H F I-487 4-fluorocinnamyl H Cl H F I-4884-bromocinnamyl H Cl H F I-489 4-trifluoromethylcinnamyl H Cl H F I-4904-trifluoromethoxycinnamyl H Cl H F I-491 4-pentafluoroethoxycinnamyl HCl H F I-492 4-methoxycinnamyl H Cl H F I-493 4-ethoxycinnamyl H Cl H FI-494 4-cyanocinnamyl H Cl H F I-495 3-(6-chloro-pyridin-3-yl)-allyl HCl H F I-496 3-(4-chlorophenyl)-but-2-enyl H Cl H F I-4973-(4-chlorophenyl)-3-fluoro- H Cl H F allyl I-4983-chloro-4-fluoro-cinnamyl H Cl H F I-499 3,5-dichloro-cinnamyl H Cl H FI-500 5-phenyl-penta-2,4-dienyl H Cl H F I-5014-isopropyloxycarbonylamino- H Cl H F cinnamyl I-5023-naphthalen-2-yl-allyl H Cl H F I-503 3-(5-trifluoromethyl-pyridin-2- HCl H F yl)-allyl I-504 3-(5-chloro-pyridin-2-yl)-allyl H Cl H F I-5053-pyridin-4-yl-allyl H Cl H F I-506 3-(2-Chloro-pyridin-4-yl)-allyl H ClH F I-507 4-chlorobenzyl H H Cl F I-508 Cinnamyl H H Cl F I-5094-chlorocinnamyl H H Cl F I-510 4-fluorocinnamyl H H Cl F I-5114-bromocinnamyl H H Cl F I-512 4-trifluoromethylcinnamyl H H Cl F I-5134-trifluoromethoxycinnamyl H H Cl F I-514 4-pentafluoroethoxycinnamyl HH Cl F I-515 4-methoxycinnamyl H H Cl F I-516 4-ethoxycinnamyl H H Cl FI-517 4-cyanocinnamyl H H Cl F I-518 3-(6-chloro-pyridin-3-yl)-allyl H HCl F I-519 3-(4-chlorophenyl)-but-2-enyl H H Cl F I-5203-(4-chlorophenyl)-3-fluoro- H H Cl F allyl I-5213-chloro-4-fluoro-cinnamyl H H Cl F I-522 3,5-dichloro-cinnamyl H H Cl FI-523 5-phenyl-penta-2,4-dienyl H H Cl F I-5244-isopropyloxycarbonylamino- H H Cl F cinnamyl I-5253-naphthalen-2-yl-allyl H H Cl F I-526 3-(5-trifluoromethyl-pyridin-2- HH Cl F yl)-allyl I-527 3-(5-chloro-pyridin-2-yl)-allyl H H Cl F I-5283-pyridin-4-yl-allyl H H Cl F I-529 3-(2-Chloro-pyridin-4-yl)-allyl H HCl F I-530 4-chlorobenzyl H F F F I-531 Cinnamyl H F F F I-5324-chlorocinnamyl H F F F I-533 4-fluorocinnamyl H F F F I-5344-bromocinnamyl H F F F I-535 4-trifluoromethylcinnamyl H F F F I-5364-trifluoromethoxycinnamyl H F F F I-537 4-pentafluoroethoxycinnamyl H FF F I-538 4-methoxycinnamyl H F F F I-539 4-ethoxycinnamyl H F F F I-5404-cyanocinnamyl H F F F I-541 3-(6-chloro-pyridin-3-yl)-allyl H F F FI-542 3-(4-chlorophenyl)-but-2-enyl H F F F I-5433-(4-chlorophenyl)-3-fluoro- H F F F allyl I-5443-chloro-4-fluoro-cinnamyl H F F F I-545 3,5-dichloro-cinnamyl H F F FI-546 5-phenyl-penta-2,4-dienyl H F F F I-5474-isopropyloxycarbonylamino- H F F F cinnamyl I-5483-naphthalen-2-yl-allyl H F F F I-549 3-(5-trifluoromethyl-pyridin-2- HF F F yl)-allyl I-550 3-(5-chloro-pyridin-2-yl)-allyl H F F F I-5513-pyridin-4-yl-allyl H F F F I-552 3-(2-Chloro-pyridin-4-yl)-allyl H F FF I-553 4-chlorobenzyl F H F F I-554 Cinnamyl F H F F I-5554-chlorocinnamyl F H F F I-556 4-fluorocinnamyl F H F F I-5574-bromocinnamyl F H F F I-558 4-trifluoromethylcinnamyl F H F F I-5594-trifluoromethoxycinnamyl F H F F I-560 4-pentafluoroethoxycinnamyl F HF F I-561 4-methoxycinnamyl F H F F I-562 4-ethoxycinnamyl F H F F I-5634-cyanocinnamyl F H F F I-564 3-(6-chloro-pyridin-3-yl)-allyl F H F FI-565 3-(4-chlorophenyl)-but-2-enyl F H F F I-5663-(4-chlorophenyl)-3-fluoro- F H F F allyl I-5673-chloro-4-fluoro-cinnamyl F H F F I-568 3,5-dichloro-cinnamyl F H F FI-569 5-phenyl-penta-2,4-dienyl F H F F I-5704-isopropyloxycarbonylamino- F H F F cinnamyl I-5713-naphthalen-2-yl-allyl F H F F I-572 3-(5-trifluoromethyl-pyridin-2- FH F F yl)-allyl I-573 3-(5-chloro-pyridin-2-yl)-allyl F H F F I-5743-pyridin-4-yl-allyl F H F F I-575 3-(2-Chloro-pyridin-4-yl)-allyl F H FF I-576 4-chlorobenzyl F F H F I-577 Cinnamyl F F H F I-5784-chlorocinnamyl F F H F I-579 4-fluorocinnamyl F F H F I-5804-bromocinnamyl F F H F I-581 4-trifluoromethylcinnamyl F F H F I-5824-trifluoromethoxycinnamyl F F H F I-583 4-pentafluoroethoxycinnamyl F FH F I-584 4-methoxycinnamyl F F H F I-585 4-ethoxycinnamyl F F H F I-5864-cyanocinnamyl F F H F I-587 3-(6-chloro-pyridin-3-yl)-allyl F F H FI-588 3-(4-chlorophenyl)-but-2-enyl F F H F I-5893-(4-chlorophenyl)-3-fluoro- F F H F allyl I-5903-chloro-4-fluoro-cinnamyl F F H F I-591 3,5-dichloro-cinnamyl F F H FI-592 5-phenyl-penta-2,4-dienyl F F H F I-5934-isopropyloxycarbonylamino- F F H F cinnamyl I-5943-naphthalen-2-yl-allyl F F H F I-595 3-(5-trifluoromethyl-pyridin-2- FF H F yl)-allyl I-596 3-(5-chloro-pyridin-2-yl)-allyl F F H F I-5973-pyridin-4-yl-allyl F F H F I-598 3-(2-Chloro-pyridin-4-yl)-allyl F F HF I-599 4-chlorobenzyl F F F H I-600 Cinnamyl F F F H I-6014-chlorocinnamyl F F F H I-602 4-fluorocinnamyl F F F H I-6034-bromocinnamyl F F F H I-604 4-trifluoromethylcinnamyl F F F H I-6054-trifluoromethoxycinnamyl F F F H I-606 4-pentafluoroethoxycinnamyl F FF H I-607 4-methoxycinnamyl F F F H I-608 4-ethoxycinnamyl F F F H I-6094-cyanocinnamyl F F F H I-610 3-(6-chloro-pyridin-3-yl)-allyl F F F HI-611 3-(4-chlorophenyl)-but-2-enyl F F F H I-6123-(4-chlorophenyl)-3-fluoro- F F F H allyl I-6133-chloro-4-fluoro-cinnamyl F F F H I-614 3,5-dichloro-cinnamyl F F F HI-615 5-phenyl-penta-2,4-dienyl F F F H I-6164-isopropyloxycarbonylamino- F F F H cinnamyl I-6173-naphthalen-2-yl-allyl F F F H I-618 3-(5-trifluoromethyl-pyridin-2- FF F H yl)-allyl I-619 3-(5-chloro-pyridin-2-yl)-allyl F F F H I-6203-pyridin-4-yl-allyl F F F H I-621 3-(2-Chloro-pyridin-4-yl)-allyl F F FH I-622 4-chlorobenzyl H Cl Cl Cl I-623 Cinnamyl H Cl Cl Cl I-6244-chlorocinnamyl H Cl Cl Cl I-625 4-fluorocinnamyl H Cl Cl Cl I-6264-bromocinnamyl H Cl Cl Cl I-627 4-trifluoromethylcinnamyl H Cl Cl ClI-628 4-trifluoromethoxycinnamyl H Cl Cl Cl I-6294-pentafluoroethoxycinnamyl H Cl Cl Cl I-630 4-methoxycinnamyl H Cl ClCl I-631 4-ethoxycinnamyl H Cl Cl Cl I-632 4-cyanocinnamyl H Cl Cl ClI-633 3-(6-chloro-pyridin-3-yl)-allyl H Cl Cl Cl I-6343-(4-chlorophenyl)-but-2-enyl H Cl Cl Cl I-6353-(4-chlorophenyl)-3-fluoro- H Cl Cl Cl allyl I-6363-chloro-4-fluoro-cinnamyl H Cl Cl Cl I-637 3,5-dichloro-cinnamyl H ClCl Cl I-638 5-phenyl-penta-2,4-dienyl H Cl Cl Cl I-6394-isopropyloxycarbonylamino- H Cl Cl Cl cinnamyl I-6403-naphthalen-2-yl-allyl H Cl Cl Cl I-641 3-(5-trifluoromethyl-pyridin-2-H Cl Cl Cl yl)-allyl I-642 3-(5-chloro-pyridin-2-yl)-allyl H Cl Cl ClI-643 3-pyridin-4-yl-allyl H Cl Cl Cl I-6443-(2-Chloro-pyridin-4-yl)-allyl H Cl Cl Cl I-645 4-chlorobenzyl Cl H ClCl I-646 Cinnamyl Cl H Cl Cl I-647 4-chlorocinnamyl Cl H Cl Cl I-6484-fluorocinnamyl Cl H Cl Cl I-649 4-bromocinnamyl Cl H Cl Cl I-6504-trifluoromethylcinnamyl Cl H Cl Cl I-651 4-trifluoromethoxycinnamyl ClH Cl Cl I-652 4-pentafluoroethoxycinnamyl Cl H Cl Cl I-6534-methoxycinnamyl Cl H Cl Cl I-654 4-ethoxycinnamyl Cl H Cl Cl I-6554-cyanocinnamyl Cl H Cl Cl I-656 3-(6-chloro-pyridin-3-yl)-allyl Cl H ClCl I-657 3-(4-chlorophenyl)-but-2-enyl Cl H Cl Cl I-6583-(4-chlorophenyl)-3-fluoro- Cl H Cl Cl allyl I-6593-chloro-4-fluoro-cinnamyl Cl H Cl Cl I-660 3,5-dichloro-cinnamyl Cl HCl Cl I-661 5-phenyl-penta-2,4-dienyl Cl H Cl Cl I-6624-isopropyloxycarbonylamino- Cl H Cl Cl cinnamyl I-6633-naphthalen-2-yl-allyl Cl H Cl Cl I-664 3-(5-trifluoromethyl-pyridin-2-Cl H Cl Cl yl)-allyl I-665 3-(5-chloro-pyridin-2-yl)-allyl Cl H Cl ClI-666 3-pyridin-4-yl-allyl Cl H Cl Cl I-6673-(2-Chloro-pyridin-4-yl)-allyl Cl H Cl Cl I-668 4-chlorobenzyl Cl Cl HCl I-669 Cinnamyl Cl Cl H Cl I-670 4-chlorocinnamyl Cl Cl H Cl I-6714-fluorocinnamyl Cl Cl H Cl I-672 4-bromocinnamyl Cl Cl H Cl I-6734-trifluoromethylcinnamyl Cl Cl H Cl I-674 4-trifluoromethoxycinnamyl ClCl H Cl I-675 4-pentafluoroethoxycinnamyl Cl Cl H Cl I-6764-methoxycinnamyl Cl Cl H Cl I-677 4-ethoxycinnamyl Cl Cl H Cl I-6784-cyanocinnamyl Cl Cl H Cl I-679 3-(6-chloro-pyridin-3-yl)-allyl Cl Cl HCl I-680 3-(4-chlorophenyl)-but-2-enyl Cl Cl H Cl I-6813-(4-chlorophenyl)-3-fluoro- Cl Cl H Cl allyl I-6823-chloro-4-fluoro-cinnamyl Cl Cl H Cl I-683 3,5-dichloro-cinnamyl Cl ClH Cl I-684 5-phenyl-penta-2,4-dienyl Cl Cl H Cl I-6854-isopropyloxycarbonylamino- Cl Cl H Cl cinnamyl I-6863-naphthalen-2-yl-allyl Cl Cl H Cl I-687 3-(5-trifluoromethyl-pyridin-2-Cl Cl H Cl yl)-allyl I-688 3-(5-chloro-pyridin-2-yl)-allyl Cl Cl H ClI-689 3-pyridin-4-yl-allyl Cl Cl H Cl I-6903-(2-Chloro-pyridin-4-yl)-allyl Cl Cl H Cl I-691 4-chlorobenzyl Cl Cl ClH I-692 Cinnamyl Cl Cl Cl H I-693 4-chlorocinnamyl Cl Cl Cl H I-6944-fluorocinnamyl Cl Cl Cl H I-695 4-bromocinnamyl Cl Cl Cl H I-6964-trifluoromethylcinnamyl Cl Cl Cl H I-697 4-trifluoromethoxycinnamyl ClCl Cl H I-698 4-pentafluoroethoxycinnamyl Cl Cl Cl H I-6994-methoxycinnamyl Cl Cl Cl H I-700 4-ethoxycinnamyl Cl Cl Cl H I-7014-cyanocinnamyl Cl Cl Cl H I-702 3-(6-chloro-pyridin-3-yl)-allyl Cl ClCl H I-703 3-(4-chlorophenyl)-but-2-enyl Cl Cl Cl H I-7043-(4-chlorophenyl)-3-fluoro- Cl Cl Cl H allyl I-7053-chloro-4-fluoro-cinnamyl Cl Cl Cl H I-706 3,5-dichloro-cinnamyl Cl ClCl H I-707 5-phenyl-penta-2,4-dienyl Cl Cl Cl H I-7084-isopropyloxycarbonylamino- Cl Cl Cl H cinnamyl I-7093-naphthalen-2-yl-allyl Cl Cl Cl H I-710 3-(5-trifluoromethyl-pyridin-2-Cl Cl Cl H yl)-allyl I-711 3-(5-chloro-pyridin-2-yl)-allyl Cl Cl Cl HI-712 3-pyridin-4-yl-allyl Cl Cl Cl H I-7133-(2-Chloro-pyridin-4-yl)-allyl Cl Cl Cl H I-714 4-chlorobenzyl Cl Cl ClCl I-715 Cinnamyl Cl Cl Cl Cl I-716 4-chlorocinnamyl Cl Cl Cl Cl I-7174-fluorocinnamyl Cl Cl Cl Cl I-718 4-bromocinnamyl Cl Cl Cl Cl I-7194-trifluoromethylcinnamyl Cl Cl Cl Cl I-720 4-trifluoromethoxycinnamylCl Cl Cl Cl I-721 4-pentafluoroethoxycinnamyl Cl Cl Cl Cl I-7224-methoxycinnamyl Cl Cl Cl Cl I-723 4-ethoxycinnamyl Cl Cl Cl Cl I-7244-cyanocinnamyl Cl Cl Cl Cl I-725 3-(6-chloro-pyridin-3-yl)-allyl Cl ClCl Cl I-726 3-(4-chlorophenyl)-but-2-enyl Cl Cl Cl Cl I-7273-(4-chlorophenyl)-3-fluoro- Cl Cl Cl Cl allyl I-7283-chloro-4-fluoro-cinnamyl Cl Cl Cl Cl I-729 3,5-dichloro-cinnamyl Cl ClCl Cl I-730 5-phenyl-penta-2,4-dienyl Cl Cl Cl Cl I-7314-isopropyloxycarbonylamino- Cl Cl Cl Cl cinnamyl I-7323-naphthalen-2-yl-allyl Cl Cl Cl Cl I-7333-(5-trifluoromethyl-pyridin-2- Cl Cl Cl Cl yl)-allyl I-7343-(5-chloro-pyridin-2-yl)-allyl Cl Cl Cl Cl I-735 3-pyridin-4-yl-allylCl Cl Cl Cl I-736 3-(2-Chloro-pyridin-4-yl)-allyl Cl Cl Cl Cl I-7374-chlorobenzyl F F F F I-738 Cinnamyl F F F F I-739 4-chlorocinnamyl F FF F I-740 4-fluorocinnamyl F F F F I-741 4-bromocinnamyl F F F F I-7424-trifluoromethylcinnamyl F F F F I-743 4-trifluoromethoxycinnamyl F F FF I-744 4-pentafluoroethoxycinnamyl F F F F I-745 4-methoxycinnamyl F FF F I-746 4-ethoxycinnamyl F F F F I-747 4-cyanocinnamyl F F F F I-7483-(6-chloro-pyridin-3-yl)-allyl F F F F I-7493-(4-chlorophenyl)-but-2-enyl F F F F I-750 3-(4-chlorophenyl)-3-fluoro-F F F F allyl I-751 3-chloro-4-fluoro-cinnamyl F F F F I-7523,5-dichloro-cinnamyl F F F F I-753 5-phenyl-penta-2,4-dienyl F F F FI-754 4-isopropyloxycarbonylamino- F F F F cinnamyl I-7553-naphthalen-2-yl-allyl F F F F I-756 3-(5-trifluoromethyl-pyridin-2- FF F F yl)-allyl I-757 3-(5-chloro-pyridin-2-yl)-allyl F F F F I-7583-pyridin-4-yl-allyl F F F F I-759 3-(2-Chloro-pyridin-4-yl)-allyl F F FF I-760 4-chlorobenzyl H F H F I-761 Cinnamyl H F H F I-7624-chlorocinnamyl H F H F I-763 4-fluorocinnamyl H F H F I-7644-bromocinnamyl H F H F I-765 4-trifluoromethylcinnamyl H F H F I-7664-trifluoromethoxycinnamyl H F H F I-767 4-pentafluoroethoxycinnamyl H FH F I-768 4-methoxycinnamyl H F H F I-769 4-ethoxycinnamyl H F H F I-7704-cyanocinnamyl H F H F I-771 3-(6-chloro-pyridin-3-yl)-allyl H F H FI-772 3-(4-chlorophenyl)-but-2-enyl H F H F I-7733-(4-chlorophenyl)-3-fluoro- H F H F allyl I-7743-chloro-4-fluoro-cinnamyl H F H F I-775 3,5-dichloro-cinnamyl H F H FI-776 5-phenyl-penta-2,4-dienyl H F H F I-7774-isopropyloxycarbonylamino- H F H F cinnamyl I-7783-naphthalen-2-yl-allyl H F H F I-779 3-(5-trifluoromethyl-pyridin-2- HF H F yl)-allyl I-780 3-(5-chloro-pyridin-2-yl)-allyl H F H F I-7813-pyridin-4-yl-allyl H F H F I-782 3-(2-Chloro-pyridin-4-yl)-allyl H F HF I-783 4-chlorobenzyl H F F H I-784 Cinnamyl H F F H I-7854-chlorocinnamyl H F F H I-786 4-fluorocinnamyl H F F H I-7874-bromocinnamyl H F F H I-788 4-trifluoromethylcinnamyl H F F H I-7894-trifluoromethoxycinnamyl H F F H I-790 4-pentafluoroethoxycinnamyl H FF H I-791 4-methoxycinnamyl H F F H I-792 4-ethoxycinnamyl H F F H I-7934-cyanocinnamyl H F F H I-794 3-(6-chloro-pyridin-3-yl)-allyl H F F HI-795 3-(4-chlorophenyl)-but-2-enyl H F F H I-7963-(4-chlorophenyl)-3-fluoro- H F F H allyl I-7973-chloro-4-fluoro-cinnamyl H F F H I-798 3,5-dichloro-cinnamyl H F F HI-799 5-phenyl-penta-2,4-dienyl H F F H I-8004-isopropyloxycarbonylamino- H F F H cinnamyl I-8013-naphthalen-2-yl-allyl H F F H I-802 3-(5-trifluoromethyl-pyridin-2- HF F H yl)-allyl I-803 3-(5-chloro-pyridin-2-yl)-allyl H F F H I-8043-pyridin-4-yl-allyl H F F H I-805 3-(2-Chloro-pyridin-4-yl)-allyl H F FH I-806 4-chlorobenzyl H F F H I-807 Cinnamyl H H F F I-8084-chlorocinnamyl H H F F I-809 4-fluorocinnamyl H H F F I-8104-bromocinnamyl H H F F I-811 4-trifluoromethylcinnamyl H H F F I-8124-trifluoromethoxycinnamyl H H F F I-813 4-pentafluoroethoxycinnamyl H HF F I-814 4-methoxycinnamyl H H F F I-815 4-ethoxycinnamyl H H F F I-8164-cyanocinnamyl H H F F I-817 3-(6-chloro-pyridin-3-yl)-allyl H H F FI-818 3-(4-chlorophenyl)-but-2-enyl H H F F I-8193-(4-chlorophenyl)-3-fluoro- H H F F allyl I-8203-chloro-4-fluoro-cinnamyl H H F F I-821 3,5-dichloro-cinnamyl H H F FI-822 5-phenyl-penta-2,4-dienyl H H F F I-8234-isopropyloxycarbonylamino- H H F F cinnamyl I-8243-naphthalen-2-yl-allyl H H F F I-825 3-(5-trifluoromethyl-pyridin-2- HH F F yl)-allyl I-826 3-(5-chloro-pyridin-2-yl)-allyl H H F F I-8273-pyridin-4-yl-allyl H H F F I-828 3-(2-Chloro-pyridin-4-yl)-allyl H H FF I-829 4-chlorobenzyl H H Cl Cl I-830 Cinnamyl H H Cl Cl I-8314-chlorocinnamyl H H Cl Cl I-832 4-fluorocinnamyl H H Cl Cl I-8334-bromocinnamyl H H Cl Cl I-834 4-trifluoromethylcinnamyl H H Cl ClI-835 4-trifluoromethoxycinnamyl H H Cl Cl I-8364-pentafluoroethoxycinnamyl H H Cl Cl I-837 4-methoxycinnamyl H H Cl ClI-838 4-ethoxycinnamyl H H Cl Cl I-839 4-cyanocinnamyl H H Cl Cl I-8403-(6-chloro-pyridin-3-yl)-allyl H H Cl Cl I-8413-(4-chlorophenyl)-but-2-enyl H H Cl Cl I-8423-(4-chlorophenyl)-3-fluoro- H H Cl Cl allyl I-8433-chloro-4-fluoro-cinnamyl H H Cl Cl I-844 3,5-dichloro-cinnamyl H H ClCl I-845 5-phenyl-penta-2,4-dienyl H H Cl Cl I-8464-isopropyloxycarbonylamino- H H Cl Cl cinnamyl I-8473-naphthalen-2-yl-allyl H H Cl Cl I-848 3-(5-trifluoromethyl-pyridin-2-H H Cl Cl yl)-allyl I-849 3-(5-chloro-pyridin-2-yl)-allyl H H Cl ClI-850 3-pyridin-4-yl-allyl H H Cl Cl I-8513-(2-Chloro-pyridin-4-yl)-allyl H H Cl Cl I-852 4-chlorobenzyl H Cl Cl HI-853 Cinnamyl H Cl Cl H I-854 4-chlorocinnamyl H Cl Cl H I-8554-fluorocinnamyl H Cl Cl H I-856 4-bromocinnamyl H Cl Cl H I-8574-trifluoromethylcinnamyl H Cl Cl H I-858 4-trifluoromethoxycinnamyl HCl Cl H I-859 4-pentafluoroethoxycinnamyl H Cl Cl H I-8604-methoxycinnamyl H Cl Cl H I-861 4-ethoxycinnamyl H Cl Cl H I-8624-cyanocinnamyl H Cl Cl H I-863 3-(6-chloro-pyridin-3-yl)-allyl H Cl ClH I-864 3-(4-chlorophenyl)-but-2-enyl H Cl Cl H I-8653-(4-chlorophenyl)-3-fluoro- H Cl Cl H allyl I-8663-chloro-4-fluoro-cinnamyl H Cl Cl H I-867 3,5-dichloro-cinnamyl H Cl ClH I-868 5-phenyl-penta-2,4-dienyl H Cl Cl H I-8694-isopropyloxycarbonylamino- H Cl Cl H cinnamyl I-8703-naphthalen-2-yl-allyl H Cl Cl H I-871 3-(5-trifluoromethyl-pyridin-2-H Cl Cl H yl)-allyl I-872 3-(5-chloro-pyridin-2-yl)-allyl H Cl Cl HI-873 3-pyridin-4-yl-allyl H Cl Cl H I-8743-(2-Chloro-pyridin-4-yl)-allyl H Cl Cl H I-875 4-chlorobenzyl H Cl H ClI-876 Cinnamyl H Cl H Cl I-877 4-chlorocinnamyl H Cl H Cl I-8784-fluorocinnamyl H Cl H Cl I-879 4-bromocinnamyl H Cl H Cl I-8804-trifluoromethylcinnamyl H Cl H Cl I-881 4-trifluoromethoxycinnamyl HCl H Cl I-882 4-pentafluoroethoxycinnamyl H Cl H Cl I-8834-methoxycinnamyl H Cl H Cl I-884 4-ethoxycinnamyl H Cl H Cl I-8854-cyanocinnamyl H Cl H Cl I-886 3-(6-chloro-pyridin-3-yl)-allyl H Cl HCl I-887 3-(4-chlorophenyl)-but-2-enyl H Cl H Cl I-8883-(4-chlorophenyl)-3-fluoro- H Cl H Cl allyl I-8893-chloro-4-fluoro-cinnamyl H Cl H Cl I-890 3,5-dichloro-cinnamyl H Cl HCl I-891 5-phenyl-penta-2,4-dienyl H Cl H Cl I-8924-isopropyloxycarbonylamino- H Cl H Cl cinnamyl I-8933-naphthalen-2-yl-allyl H Cl H Cl I-894 3-(5-trifluoromethyl-pyridin-2-H Cl H Cl yl)-allyl I-895 3-(5-chloro-pyridin-2-yl)-allyl H Cl H ClI-896 3-pyridin-4-yl-allyl H Cl H Cl I-8973-(2-Chloro-pyridin-4-yl)-allyl H Cl H Cl I-898 4-chlorobenzyl H H CH₃ HI-899 Cinnamyl H H CH₃ H I-900 4-chlorocinnamyl H H CH₃ H I-9014-fluorocinnamyl H H CH₃ H I-902 4-bromocinnamyl H H CH₃ H I-9034-trifluoromethylcinnamyl H H CH₃ H I-904 4-trifluoromethoxycinnamyl H HCH₃ H I-905 4-pentafluoroethoxycinnamyl H H CH₃ H I-9064-methoxycinnamyl H H CH₃ H I-907 4-ethoxycinnamyl H H CH₃ H I-9084-cyanocinnamyl H H CH₃ H I-909 3-(6-chloro-pyridin-3-yl)-allyl H H CH₃H I-910 3-(4-chlorophenyl)-but-2-enyl H H CH₃ H I-9113-(4-chlorophenyl)-3-fluoro- H H CH₃ H allyl I-9123-chloro-4-fluoro-cinnamyl H H CH₃ H I-913 3,5-dichloro-cinnamyl H H CH₃H I-914 5-phenyl-penta-2,4-dienyl H H CH₃ H I-9154-isopropyloxycarbonylamino- H H CH₃ H cinnamyl I-9163-naphthalen-2-yl-allyl H H CH₃ H I-917 3-(5-trifluoromethyl-pyridin-2-H H CH₃ H yl)-allyl I-918 3-(5-chloro-pyridin-2-yl)-allyl H H CH₃ HI-919 3-pyridin-4-yl-allyl H H CH₃ H I-9203-(2-Chloro-pyridin-4-yl)-allyl H H CH₃ H I-921 4-chlorobenzyl H H CF₃ HI-922 Cinnamyl H H CF₃ H I-923 4-chlorocinnamyl H H CF₃ H I-9244-fluorocinnamyl H H CF₃ H I-925 4-bromocinnamyl H H CF₃ H I-9264-trifluoromethylcinnamyl H H CF₃ H I-927 4-trifluoromethoxycinnamyl H HCF₃ H I-928 4-pentafluoroethoxycinnamyl H H CF₃ H I-9294-methoxycinnamyl H H CF₃ H I-930 4-ethoxycinnamyl H H CF₃ H I-9314-cyanocinnamyl H H CF₃ H I-932 3-(6-chloro-pyridin-3-yl)-allyl H H CF₃H I-933 3-(4-chlorophenyl)-but-2-enyl H H CF₃ H I-9343-(4-chlorophenyl)-3-fluoro- H H CF₃ H allyl I-9353-chloro-4-fluoro-cinnamyl H H CF₃ H I-936 3,5-dichloro-cinnamyl H H CF₃H I-937 5-phenyl-penta-2,4-dienyl H H CF₃ H I-9384-isopropyloxycarbonylamino- H H CF₃ H cinnamyl I-9393-naphthalen-2-yl-allyl H H CF₃ H I-940 3-(5-trifluoromethyl-pyridin-2-H H CF₃ H yl)-allyl I-941 3-(5-chloro-pyridin-2-yl)-allyl H H CF₃ HI-942 3-pyridin-4-yl-allyl H H CF₃ H I-9433-(2-Chloro-pyridin-4-yl)-allyl H H CF₃ H I-944 4-chlorobenzyl H H OCH₃H I-945 Cinnamyl H H OCH₃ H I-946 4-chlorocinnamyl H H OCH₃ H I-9474-fluorocinnamyl H H OCH₃ H I-948 4-bromocinnamyl H H OCH₃ H I-9494-trifluoromethylcinnamyl H H OCH₃ H I-950 4-trifluoromethoxycinnamyl HH OCH₃ H I-951 4-pentafluoroethoxycinnamyl H H OCH₃ H I-9524-methoxycinnamyl H H OCH₃ H I-953 4-ethoxycinnamyl H H OCH₃ H I-9544-cyanocinnamyl H H OCH₃ H I-955 3-(6-chloro-pyridin-3-yl)-allyl H HOCH₃ H I-956 3-(4-chlorophenyl)-but-2-enyl H H OCH₃ H I-9573-(4-chlorophenyl)-3-fluoro- H H OCH₃ H allyl I-9583-chloro-4-fluoro-cinnamyl H H OCH₃ H I-959 3,5-dichloro-cinnamyl H HOCH₃ H I-960 5-phenyl-penta-2,4-dienyl H H OCH₃ H I-9614-isopropyloxycarbonylamino- H H OCH₃ H cinnamyl I-9623-naphthalen-2-yl-allyl H H OCH₃ H I-963 3-(5-trifluoromethyl-pyridin-2-H H OCH₃ H yl)-allyl I-964 3-(5-chloro-pyridin-2-yl)-allyl H H OCH₃ HI-965 3-pyridin-4-yl-allyl H H OCH₃ H I-9663-(2-Chloro-pyridin-4-yl)-allyl H H OCH₃ H I-967 4-chlorobenzyl H HCO₂CH₃ H I-968 Cinnamyl H H CO₂CH₃ H I-969 4-chlorocinnamyl H H CO₂CH₃ HI-970 4-fluorocinnamyl H H CO₂CH₃ H I-971 4-bromocinnamyl H H CO₂CH₃ HI-972 4-trifluoromethylcinnamyl H H CO₂CH₃ H I-9734-trifluoromethoxycinnamyl H H CO₂CH₃ H I-9744-pentafluoroethoxycinnamyl H H CO₂CH₃ H I-975 4-methoxycinnamyl H HCO₂CH₃ H I-976 4-ethoxycinnamyl H H CO₂CH₃ H I-977 4-cyanocinnamyl H HCO₂CH₃ H I-978 3-(6-chloro-pyridin-3-yl)-allyl H H CO₂CH₃ H I-9793-(4-chlorophenyl)-but-2-enyl H H CO₂CH₃ H I-9803-(4-chlorophenyl)-3-fluoro- H H CO₂CH₃ H allyl I-9813-chloro-4-fluoro-cinnamyl H H CO₂CH₃ H I-982 3,5-dichloro-cinnamyl H HCO₂CH₃ H I-983 5-phenyl-penta-2,4-dienyl H H CO₂CH₃ H I-9844-isopropyloxycarbonylamino- H H CO₂CH₃ H cinnamyl I-9853-naphthalen-2-yl-allyl H H CO₂CH₃ H I-9863-(5-trifluoromethyl-pyridin-2- H H CO₂CH₃ H yl)-allyl I-9873-(5-chloro-pyridin-2-yl)-allyl H H CO₂CH₃ H I-988 3-pyridin-4-yl-allylH H CO₂CH₃ H I-989 3-(2-Chloro-pyridin-4-yl)-allyl H H CO₂CH₃ H I-9904-chlorobenzyl CH₃ H H H I-991 Cinnamyl CH₃ H H H I-992 4-chlorocinnamylCH₃ H H H I-993 4-fluorocinnamyl CH₃ H H H I-994 4-bromocinnamyl CH₃ H HH I-995 4-trifluoromethylcinnamyl CH₃ H H H I-9964-trifluoromethoxycinnamyl CH₃ H H H I-997 4-pentafluoroethoxycinnamylCH₃ H H H I-998 4-methoxycinnamyl CH₃ H H H I-999 4-ethoxycinnamyl CH₃ HH H I-1000 4-cyanocinnamyl CH₃ H H H I-10013-(6-chloro-pyridin-3-yl)-allyl CH₃ H H H I-10023-(4-chlorophenyl)-but-2-enyl CH₃ H H H I-10033-(4-chlorophenyl)-3-fluoro- CH₃ H H H allyl I-10043-chloro-4-fluoro-cinnamyl CH₃ H H H I-1005 3,5-dichloro-cinnamyl CH₃ HH H I-1006 5-phenyl-penta-2,4-dienyl CH₃ H H H I-10074-isopropyloxycarbonylamino- CH₃ H H H cinnamyl I-10083-naphthalen-2-yl-allyl CH₃ H H H I-1009 3-(5-trifluoromethyl-pyridin-2-CH₃ H H H yl)-allyl I-1010 3-(5-chloro-pyridin-2-yl)-allyl CH₃ H H HI-1011 3-pyridin-4-yl-allyl CH₃ H H H I-10123-(2-Chloro-pyridin-4-yl)-allyl CH₃ H H H I-1013 4-chlorobenzyl H CH₃ HH I-1014 Cinnamyl H CH₃ H H I-1015 4-chlorocinnamyl H CH₃ H H I-10164-fluorocinnamyl H CH₃ H H I-1017 4-bromocinnamyl H CH₃ H H I-10184-trifluoromethylcinnamyl H CH₃ H H I-1019 4-trifluoromethoxycinnamyl HCH₃ H H I-1020 4-pentafluoroethoxycinnamyl H CH₃ H H I-10214-methoxycinnamyl H CH₃ H H I-1022 4-ethoxycinnamyl H CH₃ H H I-10234-cyanocinnamyl H CH₃ H H I-1024 3-(6-chloro-pyridin-3-yl)-allyl H CH₃ HH I-1025 3-(4-chlorophenyl)-but-2-enyl H CH₃ H H I-10263-(4-chlorophenyl)-3-fluoro- H CH₃ H H allyl I-10273-chloro-4-fluoro-cinnamyl H CH₃ H H I-1028 3,5-dichloro-cinnamyl H CH₃H H I-1029 5-phenyl-penta-2,4-dienyl H CH₃ H H I-10304-isopropyloxycarbonylamino- H CH₃ H H cinnamyl I-10313-naphthalen-2-yl-allyl H CH₃ H H I-1032 3-(5-trifluoromethyl-pyridin-2-H CH₃ H H yl)-allyl I-1033 3-(5-chloro-pyridin-2-yl)-allyl H CH₃ H HI-1034 3-pyridin-4-yl-allyl H CH₃ H H I-10353-(2-Chloro-pyridin-4-yl)-allyl H CH₃ H H I-1036 4-chlorobenzyl H H HCH₃ I-1037 Cinnamyl H H H CH₃ I-1038 4-chlorocinnamyl H H H CH₃ I-10394-fluorocinnamyl H H H CH₃ I-1040 4-bromocinnamyl H H H CH₃ I-10414-trifluoromethylcinnamyl H H H CH₃ I-1042 4-trifluoromethoxycinnamyl HH H CH₃ I-1043 4-pentafluoroethoxycinnamyl H H H CH₃ I-10444-methoxycinnamyl H H H CH₃ I-1045 4-ethoxycinnamyl H H H CH₃ I-10464-cyanocinnamyl H H H CH₃ I-1047 3-(6-chloro-pyridin-3-yl)-allyl H H HCH₃ I-1048 3-(4-chlorophenyl)-but-2-enyl H H H CH₃ I-10493-(4-chlorophenyl)-3-fluoro- H H H CH₃ allyl I-10503-chloro-4-fluoro-cinnamyl H H H CH₃ I-1051 3,5-dichloro-cinnamyl H H HCH₃ I-1052 5-phenyl-penta-2,4-dienyl H H H CH₃ I-10534-isopropyloxycarbonylamino- H H H CH₃ cinnamyl I-10543-naphthalen-2-yl-allyl H H H CH₃ I-1055 3-(5-trifluoromethyl-pyridin-2-H H H CH₃ yl)-allyl I-1056 3-(5-chloro-pyridin-2-yl)-allyl H H H CH₃I-1057 3-pyridin-4-yl-allyl H H H CH₃ I-10583-(2-Chloro-pyridin-4-yl)-allyl H H H CH₃ I-1059 4-chlorobenzyl H CF₃ HH I-1060 Cinnamyl H CF₃ H H I-1061 4-chlorocinnamyl H CF₃ H H I-10624-fluorocinnamyl H CF₃ H H I-1063 4-bromocinnamyl H CF₃ H H I-10644-trifluoromethylcinnamyl H CF₃ H H I-1065 4-trifluoromethoxycinnamyl HCF₃ H H I-1066 4-pentafluoroethoxycinnamyl H CF₃ H H I-10674-methoxycinnamyl H CF₃ H H I-1068 4-ethoxycinnamyl H CF₃ H H I-10694-cyanocinnamyl H CF₃ H H I-1070 3-(6-chloro-pyridin-3-yl)-allyl H CF₃ HH I-1071 3-(4-chlorophenyl)-but-2-enyl H CF₃ H H I-10723-(4-chlorophenyl)-3-fluoro- H CF₃ H H allyl I-10733-chloro-4-fluoro-cinnamyl H CF₃ H H I-1074 3,5-dichloro-cinnamyl H CF₃H H I-1075 5-phenyl-penta-2,4-dienyl H CF₃ H H I-10764-isopropyloxycarbonylamino- H CF₃ H H cinnamyl I-10773-naphthalen-2-yl-allyl H CF₃ H H I-1078 3-(5-trifluoromethyl-pyridin-2-H CF₃ H H yl)-allyl I-1079 3-(5-chloro-pyridin-2-yl)-allyl H CF₃ H HI-1080 3-pyridin-4-yl-allyl H CF₃ H H I-10813-(2-Chloro-pyridin-4-yl)-allyl H CF₃ H H I-1082 4-chlorobenzyl H iPr HH I-1083 Cinnamyl H iPr H H I-1084 4-chlorocinnamyl H iPr H H I-10854-fluorocinnamyl H iPr H H I-1086 4-bromocinnamyl H iPr H H I-10874-trifluoromethylcinnamyl H iPr H H I-1088 4-trifluoromethoxycinnamyl HiPr H H I-1089 4-pentafluoroethoxycinnamyl H iPr H H I-10904-methoxycinnamyl H iPr H H I-1091 4-ethoxycinnamyl H iPr H H I-10924-cyanocinnamyl H iPr H H I-1093 3-(6-chloro-pyridin-3-yl)-allyl H iPr HH I-1094 3-(4-chlorophenyl)-but-2-enyl H iPr H H I-10953-(4-chlorophenyl)-3-fluoro- H iPr H H allyl I-10963-chloro-4-fluoro-cinnamyl H iPr H H I-1097 3,5-dichloro-cinnamyl H iPrH H I-1098 5-phenyl-penta-2,4-dienyl H iPr H H I-10994-isopropyloxycarbonylamino- H iPr H H cinnamyl I-11003-naphthalen-2-yl-allyl H iPr H H I-1101 3-(5-trifluoromethyl-pyridin-2-H iPr H H yl)-allyl I-1102 3-(5-chloro-pyridin-2-yl)-allyl H iPr H HI-1103 3-pyridin-4-yl-allyl H iPr H H I-11043-(2-Chloro-pyridin-4-yl)-allyl H iPr H H I-1105 4-chlorobenzyl H OCF₃ HH I-1106 Cinnamyl H OCF₃ H H I-1107 4-chlorocinnamyl H OCF₃ H H I-11084-fluorocinnamyl H OCF₃ H H I-1109 4-bromocinnamyl H OCF₃ H H I-11104-trifluoromethylcinnamyl H OCF₃ H H I-1111 4-trifluoromethoxycinnamyl HOCF₃ H H I-1112 4-pentafluoroethoxycinnamyl H OCF₃ H H I-11134-methoxycinnamyl H OCF₃ H H I-1114 4-ethoxycinnamyl H OCF₃ H H I-11154-cyanocinnamyl H OCF₃ H H I-1116 3-(6-chloro-pyridin-3-yl)-allyl H OCF₃H H I-1117 3-(4-chlorophenyl)-but-2-enyl H OCF₃ H H I-11183-(4-chlorophenyl)-3-fluoro- H OCF₃ H H allyl I-11193-chloro-4-fluoro-cinnamyl H OCF₃ H H I-1120 3,5-dichloro-cinnamyl HOCF₃ H H I-1121 5-phenyl-penta-2,4-dienyl H OCF₃ H H I-11224-isopropyloxycarbonylamino- H OCF₃ H H cinnamyl I-11233-naphthalen-2-yl-allyl H OCF₃ H H I-11243-(5-trifluoromethyl-pyridin-2- H OCF₃ H H yl)-allyl I-11253-(5-chloro-pyridin-2-yl)-allyl H OCF₃ H H I-1126 3-pyridin-4-yl-allyl HOCF₃ H H I-1127 3-(2-Chloro-pyridin-4-yl)-allyl H OCF₃ H H

Table II provides 1127 compounds of formula Ib

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table III provides 1127 compounds of formula Ic

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table IV provides 1127 compounds of formula Id

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table V provides 1127 compounds of formula Ie

wherein and the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) aregiven in Table 1

Table VI provides 1127 compounds of formula If

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table VII provides 1127 compounds of formula Ig

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table VIII provides 1127 compounds of formula Ih

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table IX provides 1127 compounds of formula Ii

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table X provides 1127 compounds of formula Ij

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XI provides 1127 compounds of formula Ik

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XII provides 1127 compounds of formula Il

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XIII provides 1127 compounds of formula Im

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XIV provides 1127 compounds of formula In

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XV provides 1127 compounds of formula Io

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XVI provides 1127 compounds of formula Ip

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XVII provides 1127 compounds of formula Iq

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XVIII provides 1127 compounds of formula Ir

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XIX provides 1127 compounds of formula Is

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XX provides 1127 compounds of formula It

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXI provides 1127 compounds of formula Iu

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXII provides 1127 compounds of formula Iv

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXIII provides 1127 compounds of formula Iw

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXIV provides 1127 compounds of formula Ix

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXV provides 1127 compounds of formula Iaa

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXVII provides 1127 compounds of formula Iac

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table XXVIII provides 1127 compounds of formula Iad

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table XXIX provides 1127 compounds of formula Iae

wherein and the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) aregiven in Table 1

Table XXX provides 1127 compounds of formula Iaf

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table XXXI provides 1127 compounds of formula Iag

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXII provides 1127 compounds of formula Iah

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table XXXIII provides 1127 compounds of formula Iai

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXIV provides 1127 compounds of formula Iaj

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXV provides 1127 compounds of formula Iak

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXVI provides 1127 compounds of formula Ial

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXVII provides 1127 compounds of formula Iam

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXVIII provides 1127 compounds of formula Ian

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XXXIX provides 1127 compounds of formula Iao

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XL provides 1127 compounds of formula Iap

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLI provides 1127 compounds of formula Iaq

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLII provides 1127 compounds of formula Iar

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLIII provides 1127 compounds of formula Ias

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLIV provides 1127 compounds of formula Iat

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLV provides 1127 compounds of formula Iau

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLVI provides 1127 compounds of formula lay

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLVII provides 1127 compounds of formula Iaw

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table XLVIII provides 1127 compounds of formula Iax

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table IL provides 1127 compounds of formula Iaaa

Table L provides 1127 compounds of formula Iaab

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LI provides 1127 compounds of formula Iaac

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table LII provides 1127 compounds of formula Iaad

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table LIII provides 1127 compounds of formula Iaae

wherein and the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) aregiven in Table 1

Table LIV provides 1127 compounds of formula Iaaf

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table LV provides 1127 compounds of formula Iaag

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LVI provides 1127 compounds of formula Iaah

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1

Table LVII provides 1127 compounds of formula Iaai

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LVIII provides 1127 compounds of formula Iaaj

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LIX provides 1127 compounds of formula Iaak

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LX provides 1127 compounds of formula Iaal

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXI provides 1127 compounds of formula Iaam

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXII provides 1127 compounds of formula Iaan

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXIII provides 1127 compounds of formula Iaao

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXIV provides 1127 compounds of formula Iaap

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXV provides 1127 compounds of formula Iaaq

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXVI provides 1127 compounds of formula Iaar

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXVII provides 1127 compounds of formula Iaas

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXVIII provides 1127 compounds of formula Iaat

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXIX provides 1127 compounds of formula Iaau

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXX provides 1127 compounds of formula Iaav

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.

Table LXXI provides 1127 compounds of formula Iaaw

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.Table LXXII provides 1127 compounds of formula Iaax

wherein the values of R⁸, R^(4a), R^(4b), R^(4c) and R^(4d) are given inTable 1.Table LXXIII provides 506 compounds of formula Iy

wherein the values of R⁸ and R¹ are given in Table 73.

TABLE 73 Compound No R⁸ R1 LXXIII-1 Cinnamyl 2-chloro-pyrid-4-ylLXXIII-2 4-chlorocinnamyl 2-chloro-pyrid-4-yl LXXIII-3 4-fluorocinnamyl2-chloro-pyrid-4-yl LXXIII-4 4-bromocinnamyl 2-chloro-pyrid-4-ylLXXIII-5 4-trifluoromethylcinnamyl 2-chloro-pyrid-4-yl LXXIII-64-trifluoromethoxycinnamyl 2-chloro-pyrid-4-yl LXXIII-74-pentafluoroethoxycinnamyl 2-chloro-pyrid-4-yl LXXIII-84-methoxycinnamyl 2-chloro-pyrid-4-yl LXXIII-9 4-ethoxycinnamyl2-chloro-pyrid-4-yl LXXIII-10 4-cyanocinnamyl 2-chloro-pyrid-4-ylLXXIII-11 3-(6-chloro-pyridin-3-yl)-allyl 2-chloro-pyrid-4-yl LXXIII-123-(4-chlorophenyl)-but-2-enyl 2-chloro-pyrid-4-yl LXXIII-133-(4-chlorophenyl)-3-fluoro-allyl 2-chloro-pyrid-4-yl LXXIII-143-chloro-4-fluoro-cinnamyl 2-chloro-pyrid-4-yl LXXIII-153,5-dichloro-cinnamyl 2-chloro-pyrid-4-yl LXXIII-165-phenyl-penta-2,4-dienyl 2-chloro-pyrid-4-yl LXXIII-174-isopropyloxycarbonylamino-cinnamyl 2-chloro-pyrid-4-yl LXXIII-183-naphthalen-2-yl-allyl 2-chloro-pyrid-4-yl LXXIII-193-(5-trifluoromethyl-pyridin-2-yl)-allyl 2-chloro-pyrid-4-yl LXXIII-203-(5-chloro-pyridin-2-yl)-allyl 2-chloro-pyrid-4-yl LXXIII-213-pyridin-4-yl-allyl 2-chloro-pyrid-4-yl LXXIII-223-(2-Chloro-pyridin-4-yl)-allyl 2-chloro-pyrid-4-yl LXXIII-23 Cinnamylpyrid-4-yl LXXIII-24 4-chlorocinnamyl pyrid-4-yl LXXIII-254-fluorocinnamyl pyrid-4-yl LXXIII-26 4-bromocinnamyl pyrid-4-ylLXXIII-27 4-trifluoromethylcinnamyl pyrid-4-yl LXXIII-284-trifluoromethoxycinnamyl pyrid-4-yl LXXIII-294-pentafluoroethoxycinnamyl pyrid-4-yl LXXIII-30 4-methoxycinnamylpyrid-4-yl LXXIII-31 4-ethoxycinnamyl pyrid-4-yl LXXIII-324-cyanocinnamyl pyrid-4-yl LXXIII-33 3-(6-chloro-pyridin-3-yl)-allylpyrid-4-yl LXXIII-34 3-(4-chlorophenyl)-but-2-enyl pyrid-4-yl LXXIII-353-(4-chlorophenyl)-3-fluoro-allyl pyrid-4-yl LXXIII-363-chloro-4-fluoro-cinnamyl pyrid-4-yl LXXIII-37 3,5-dichloro-cinnamylpyrid-4-yl LXXIII-38 5-phenyl-penta-2,4-dienyl pyrid-4-yl LXXIII-394-isopropyloxycarbonylamino-cinnamyl pyrid-4-yl LXXIII-403-naphthalen-2-yl-allyl pyrid-4-yl LXXIII-413-(5-trifluoromethyl-pyridin-2-yl)-allyl pyrid-4-yl LXXIII-423-(5-chloro-pyridin-2-yl)-allyl pyrid-4-yl LXXIII-433-pyridin-4-yl-allyl pyrid-4-yl LXXIII-443-(2-Chloro-pyridin-4-yl)-allyl pyrid-4-yl LXXIII-45 Cinnamyl2,6-dichloro-pyrid-4-yl LXXIII-46 4-chlorocinnamyl2,6-dichloro-pyrid-4-yl LXXIII-47 4-fluorocinnamyl2,6-dichloro-pyrid-4-yl LXXIII-48 4-bromocinnamyl2,6-dichloro-pyrid-4-yl LXXIII-49 4-trifluoromethylcinnamyl2,6-dichloro-pyrid-4-yl LXXIII-50 4-trifluoromethoxycinnamyl2,6-dichloro-pyrid-4-yl LXXIII-51 4-pentafluoroethoxycinnamyl2,6-dichloro-pyrid-4-yl LXXIII-52 4-methoxycinnamyl2,6-dichloro-pyrid-4-yl LXXIII-53 4-ethoxycinnamyl2,6-dichloro-pyrid-4-yl LXXIII-54 4-cyanocinnamyl2,6-dichloro-pyrid-4-yl LXXIII-55 3-(6-chloro-pyridin-3-yl)-allyl2,6-dichloro-pyrid-4-yl LXXIII-56 3-(4-chlorophenyl)-but-2-enyl2,6-dichloro-pyrid-4-yl LXXIII-57 3-(4-chlorophenyl)-3-fluoro-allyl2,6-dichloro-pyrid-4-yl LXXIII-58 3-chloro-4-fluoro-cinnamyl2,6-dichloro-pyrid-4-yl LXXIII-59 3,5-dichloro-cinnamyl2,6-dichloro-pyrid-4-yl LXXIII-60 5-phenyl-penta-2,4-dienyl2,6-dichloro-pyrid-4-yl LXXIII-61 4-isopropyloxycarbonylamino-cinnamyl2,6-dichloro-pyrid-4-yl LXXIII-62 3-naphthalen-2-yl-allyl2,6-dichloro-pyrid-4-yl LXXIII-633-(5-trifluoromethyl-pyridin-2-yl)-allyl 2,6-dichloro-pyrid-4-ylLXXIII-64 3-(5-chloro-pyridin-2-yl)-allyl 2,6-dichloro-pyrid-4-ylLXXIII-65 3-pyridin-4-yl-allyl 2,6-dichloro-pyrid-4-yl LXXIII-663-(2-Chloro-pyridin-4-yl)-allyl 2,6-dichloro-pyrid-4-yl LXXIII-67Cinnamyl 2-bromo-pyrid-4-yl LXXIII-68 4-chlorocinnamyl2-bromo-pyrid-4-yl LXXIII-69 4-fluorocinnamyl 2-bromo-pyrid-4-ylLXXIII-70 4-bromocinnamyl 2-bromo-pyrid-4-yl LXXIII-714-trifluoromethylcinnamyl 2-bromo-pyrid-4-yl LXXIII-724-trifluoromethoxycinnamyl 2-bromo-pyrid-4-yl LXXIII-734-pentafluoroethoxycinnamyl 2-bromo-pyrid-4-yl LXXIII-744-methoxycinnamyl 2-bromo-pyrid-4-yl LXXIII-75 4-ethoxycinnamyl2-bromo-pyrid-4-yl LXXIII-76 4-cyanocinnamyl 2-bromo-pyrid-4-ylLXXIII-77 3-(6-chloro-pyridin-3-yl)-allyl 2-bromo-pyrid-4-yl LXXIII-783-(4-chlorophenyl)-but-2-enyl 2-bromo-pyrid-4-yl LXXIII-793-(4-chlorophenyl)-3-fluoro-allyl 2-bromo-pyrid-4-yl LXXIII-803-chloro-4-fluoro-cinnamyl 2-bromo-pyrid-4-yl LXXIII-813,5-dichloro-cinnamyl 2-bromo-pyrid-4-yl LXXIII-825-phenyl-penta-2,4-dienyl 2-bromo-pyrid-4-yl LXXIII-834-isopropyloxycarbonylamino-cinnamyl 2-bromo-pyrid-4-yl LXXIII-843-naphthalen-2-yl-allyl 2-bromo-pyrid-4-yl LXXIII-853-(5-trifluoromethyl-pyridin-2-yl)-allyl 2-bromo-pyrid-4-yl LXXIII-863-(5-chloro-pyridin-2-yl)-allyl 2-bromo-pyrid-4-yl LXXIII-873-pyridin-4-yl-allyl 2-bromo-pyrid-4-yl LXXIII-883-(2-Chloro-pyridin-4-yl)-allyl 2-bromo-pyrid-4-yl LXXIII-89 Cinnamyl2-fluoro-pyrid-4-yl LXXIII-90 4-chlorocinnamyl 2-fluoro-pyrid-4-ylLXXIII-91 4-fluorocinnamyl 2-fluoro-pyrid-4-yl LXXIII-92 4-bromocinnamyl2-fluoro-pyrid-4-yl LXXIII-93 4-trifluoromethylcinnamyl2-fluoro-pyrid-4-yl LXXIII-94 4-trifluoromethoxycinnamyl2-fluoro-pyrid-4-yl LXXIII-95 4-pentafluoroethoxycinnamyl2-fluoro-pyrid-4-yl LXXIII-96 4-methoxycinnamyl 2-fluoro-pyrid-4-ylLXXIII-97 4-ethoxycinnamyl 2-fluoro-pyrid-4-yl LXXIII-98 4-cyanocinnamyl2-fluoro-pyrid-4-yl LXXIII-99 3-(6-chloro-pyridin-3-yl)-allyl2-fluoro-pyrid-4-yl LXXIII-100 3-(4-chlorophenyl)-but-2-enyl2-fluoro-pyrid-4-yl LXXIII-101 3-(4-chlorophenyl)-3-fluoro-allyl2-fluoro-pyrid-4-yl LXXIII-102 3-chloro-4-fluoro-cinnamyl2-fluoro-pyrid-4-yl LXXIII-103 3,5-dichloro-cinnamyl 2-fluoro-pyrid-4-ylLXXIII-104 5-phenyl-penta-2,4-dienyl 2-fluoro-pyrid-4-yl LXXIII-1054-isopropyloxycarbonylamino-cinnamyl 2-fluoro-pyrid-4-yl LXXIII-1063-naphthalen-2-yl-allyl 2-fluoro-pyrid-4-yl LXXIII-1073-(5-trifluoromethyl-pyridin-2-yl)-allyl 2-fluoro-pyrid-4-yl LXXIII-1083-(5-chloro-pyridin-2-yl)-allyl 2-fluoro-pyrid-4-yl LXXIII-1093-pyridin-4-yl-allyl 2-fluoro-pyrid-4-yl LXXIII-1103-(2-Chloro-pyridin-4-yl)-allyl 2-fluoro-pyrid-4-yl LXXIII-111 Cinnamyl2,6-dibromo-pyrid-4-yl LXXIII-112 4-chlorocinnamyl2,6-dibromo-pyrid-4-yl LXXIII-113 4-fluorocinnamyl2,6-dibromo-pyrid-4-yl LXXIII-114 4-bromocinnamyl 2,6-dibromo-pyrid-4-ylLXXIII-115 4-trifluoromethylcinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-1164-trifluoromethoxycinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-1174-pentafluoroethoxycinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-1184-methoxycinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-119 4-ethoxycinnamyl2,6-dibromo-pyrid-4-yl LXXIII-120 4-cyanocinnamyl 2,6-dibromo-pyrid-4-ylLXXIII-121 3-(6-chloro-pyridin-3-yl)-allyl 2,6-dibromo-pyrid-4-ylLXXIII-122 3-(4-chlorophenyl)-but-2-enyl 2,6-dibromo-pyrid-4-ylLXXIII-123 3-(4-chlorophenyl)-3-fluoro-allyl 2,6-dibromo-pyrid-4-ylLXXIII-124 3-chloro-4-fluoro-cinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-1253,5-dichloro-cinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-1265-phenyl-penta-2,4-dienyl 2,6-dibromo-pyrid-4-yl LXXIII-1274-isopropyloxycarbonylamino-cinnamyl 2,6-dibromo-pyrid-4-yl LXXIII-1283-naphthalen-2-yl-allyl 2,6-dibromo-pyrid-4-yl LXXIII-1293-(5-trifluoromethyl-pyridin-2-yl)-allyl 2,6-dibromo-pyrid-4-ylLXXIII-130 3-(5-chloro-pyridin-2-yl)-allyl 2,6-dibromo-pyrid-4-ylLXXIII-131 3-pyridin-4-yl-allyl 2,6-dibromo-pyrid-4-yl LXXIII-1323-(2-Chloro-pyridin-4-yl)-allyl 2,6-dibromo-pyrid-4-yl LXXIII-133Cinnamyl 2-trifluoromethyl-pyrid-4-yl LXXIII-134 4-chlorocinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-135 4-fluorocinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-136 4-bromocinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-137 4-trifluoromethylcinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-138 4-trifluoromethoxycinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-139 4-pentafluoroethoxycinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-140 4-methoxycinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-141 4-ethoxycinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-142 4-cyanocinnamyl2-trifluoromethyl-pyrid-4-yl LXXIII-143 3-(6-chloro-pyridin-3-yl)-allyl2-trifluoromethyl-pyrid-4-yl LXXIII-144 3-(4-chlorophenyl)-but-2-enyl2-trifluoromethyl-pyrid-4-yl LXXIII-1453-(4-chlorophenyl)-3-fluoro-allyl 2-trifluoromethyl-pyrid-4-ylLXXIII-146 3-chloro-4-fluoro-cinnamyl 2-trifluoromethyl-pyrid-4-ylLXXIII-147 3,5-dichloro-cinnamyl 2-trifluoromethyl-pyrid-4-yl LXXIII-1485-phenyl-penta-2,4-dienyl 2-trifluoromethyl-pyrid-4-yl LXXIII-1494-isopropyloxycarbonylamino-cinnamyl 2-trifluoromethyl-pyrid-4-ylLXXIII-150 3-naphthalen-2-yl-allyl 2-trifluoromethyl-pyrid-4-ylLXXIII-151 3-(5-trifluoromethyl-pyridin-2-yl)-allyl2-trifluoromethyl-pyrid-4-yl LXXIII-152 3-(5-chloro-pyridin-2-yl)-allyl2-trifluoromethyl-pyrid-4-yl LXXIII-153 3-pyridin-4-yl-allyl2-trifluoromethyl-pyrid-4-yl LXXIII-154 3-(2-Chloro-pyridin-4-yl)-allyl2-trifluoromethyl-pyrid-4-yl LXXIII-155 Cinnamyl 2,6-difluoro-pyrid-4-ylLXXIII-156 4-chlorocinnamyl 2,6-difluoro-pyrid-4-yl LXXIII-1574-fluorocinnamyl 2,6-difluoro-pyrid-4-yl LXXIII-158 4-bromocinnamyl2,6-difluoro-pyrid-4-yl LXXIII-159 4-trifluoromethylcinnamyl2,6-difluoro-pyrid-4-yl LXXIII-160 4-trifluoromethoxycinnamyl2,6-difluoro-pyrid-4-yl LXXIII-161 4-pentafluoroethoxycinnamyl2,6-difluoro-pyrid-4-yl LXXIII-162 4-methoxycinnamyl2,6-difluoro-pyrid-4-yl LXXIII-163 4-ethoxycinnamyl2,6-difluoro-pyrid-4-yl LXXIII-164 4-cyanocinnamyl2,6-difluoro-pyrid-4-yl LXXIII-165 3-(6-chloro-pyridin-3-yl)-allyl2,6-difluoro-pyrid-4-yl LXXIII-166 3-(4-chlorophenyl)-but-2-enyl2,6-difluoro-pyrid-4-yl LXXIII-167 3-(4-chlorophenyl)-3-fluoro-allyl2,6-difluoro-pyrid-4-yl LXXIII-168 3-chloro-4-fluoro-cinnamyl2,6-difluoro-pyrid-4-yl LXXIII-169 3,5-dichloro-cinnamyl2,6-difluoro-pyrid-4-yl LXXIII-170 5-phenyl-penta-2,4-dienyl2,6-difluoro-pyrid-4-yl LXXIII-171 4-isopropyloxycarbonylamino-cinnamyl2,6-difluoro-pyrid-4-yl LXXIII-172 3-naphthalen-2-yl-allyl2,6-difluoro-pyrid-4-yl LXXIII-1733-(5-trifluoromethyl-pyridin-2-yl)-allyl 2,6-difluoro-pyrid-4-ylLXXIII-174 3-(5-chloro-pyridin-2-yl)-allyl 2,6-difluoro-pyrid-4-ylLXXIII-175 3-pyridin-4-yl-allyl 2,6-difluoro-pyrid-4-yl LXXIII-1763-(2-Chloro-pyridin-4-yl)-allyl 2,6-difluoro-pyrid-4-yl LXXIII-177Cinnamyl methyl LXXIII-178 4-chlorocinnamyl methyl LXXIII-1794-fluorocinnamyl methyl LXXIII-180 4-bromocinnamyl methyl LXXIII-1814-trifluoromethylcinnamyl methyl LXXIII-182 4-trifluoromethoxycinnamylmethyl LXXIII-183 4-pentafluoroethoxycinnamyl methyl LXXIII-1844-methoxycinnamyl methyl LXXIII-185 4-ethoxycinnamyl methyl LXXIII-1864-cyanocinnamyl methyl LXXIII-187 3-(6-chloro-pyridin-3-yl)-allyl methylLXXIII-188 3-(4-chlorophenyl)-but-2-enyl methyl LXXIII-1893-(4-chlorophenyl)-3-fluoro-allyl methyl LXXIII-1903-chloro-4-fluoro-cinnamyl methyl LXXIII-191 3,5-dichloro-cinnamylmethyl LXXIII-192 5-phenyl-penta-2,4-dienyl methyl LXXIII-1934-isopropyloxycarbonylamino-cinnamyl methyl LXXIII-1943-naphthalen-2-yl-allyl methyl LXXIII-1953-(5-trifluoromethyl-pyridin-2-yl)-allyl methyl LXXIII-1963-(5-chloro-pyridin-2-yl)-allyl methyl LXXIII-197 3-pyridin-4-yl-allylmethyl LXXIII-198 3-(2-Chloro-pyridin-4-yl)-allyl methyl LXXIII-199Cinnamyl methoxyethyl LXXIII-200 4-chlorocinnamyl methoxyethylLXXIII-201 4-fluorocinnamyl methoxyethyl LXXIII-202 4-bromocinnamylmethoxyethyl LXXIII-203 4-trifluoromethylcinnamyl methoxyethylLXXIII-204 4-trifluoromethoxycinnamyl methoxyethyl LXXIII-2054-pentafluoroethoxycinnamyl methoxyethyl LXXIII-206 4-methoxycinnamylmethoxyethyl LXXIII-207 4-ethoxycinnamyl methoxyethyl LXXIII-2084-cyanocinnamyl methoxyethyl LXXIII-209 3-(6-chloro-pyridin-3-yl)-allylmethoxyethyl LXXIII-210 3-(4-chlorophenyl)-but-2-enyl methoxyethylLXXIII-211 3-(4-chlorophenyl)-3-fluoro-allyl methoxyethyl LXXIII-2123-chloro-4-fluoro-cinnamyl methoxyethyl LXXIII-213 3,5-dichloro-cinnamylmethoxyethyl LXXIII-214 5-phenyl-penta-2,4-dienyl methoxyethylLXXIII-215 4-isopropyloxycarbonylamino-cinnamyl methoxyethyl LXXIII-2163-naphthalen-2-yl-allyl methoxyethyl LXXIII-2173-(5-trifluoromethyl-pyridin-2-yl)-allyl methoxyethyl LXXIII-2183-(5-chloro-pyridin-2-yl)-allyl methoxyethyl LXXIII-2193-pyridin-4-yl-allyl methoxyethyl LXXIII-2203-(2-Chloro-pyridin-4-yl)-allyl methoxyethyl LXXIII-221 Cinnamyl2,2,2-trifluoroethyl LXXIII-222 4-chlorocinnamyl 2,2,2-trifluoroethylLXXIII-223 4-fluorocinnamyl 2,2,2-trifluoroethyl LXXIII-2244-bromocinnamyl 2,2,2-trifluoroethyl LXXIII-2254-trifluoromethylcinnamyl 2,2,2-trifluoroethyl LXXIII-2264-trifluoromethoxycinnamyl 2,2,2-trifluoroethyl LXXIII-2274-pentafluoroethoxycinnamyl 2,2,2-trifluoroethyl LXXIII-2284-methoxycinnamyl 2,2,2-trifluoroethyl LXXIII-229 4-ethoxycinnamyl2,2,2-trifluoroethyl LXXIII-230 4-cyanocinnamyl 2,2,2-trifluoroethylLXXIII-231 3-(6-chloro-pyridin-3-yl)-allyl 2,2,2-trifluoroethylLXXIII-232 3-(4-chlorophenyl)-but-2-enyl 2,2,2-trifluoroethyl LXXIII-2333-(4-chlorophenyl)-3-fluoro-allyl 2,2,2-trifluoroethyl LXXIII-2343-chloro-4-fluoro-cinnamyl 2,2,2-trifluoroethyl LXXIII-2353,5-dichloro-cinnamyl 2,2,2-trifluoroethyl LXXIII-2365-phenyl-penta-2,4-dienyl 2,2,2-trifluoroethyl LXXIII-2374-isopropyloxycarbonylamino-cinnamyl 2,2,2-trifluoroethyl LXXIII-2383-naphthalen-2-yl-allyl 2,2,2-trifluoroethyl LXXIII-2393-(5-trifluoromethyl-pyridin-2-yl)-allyl 2,2,2-trifluoroethyl LXXIII-2403-(5-chloro-pyridin-2-yl)-allyl 2,2,2-trifluoroethyl LXXIII-2413-pyridin-4-yl-allyl 2,2,2-trifluoroethyl LXXIII-2423-(2-Chloro-pyridin-4-yl)-allyl 2,2,2-trifluoroethyl LXXIII-243 Cinnamylmethoxy LXXIII-244 4-chlorocinnamyl methoxy LXXIII-245 4-fluorocinnamylmethoxy LXXIII-246 4-bromocinnamyl methoxy LXXIII-2474-trifluoromethylcinnamyl methoxy LXXIII-248 4-trifluoromethoxycinnamylmethoxy LXXIII-249 4-pentafluoroethoxycinnamyl methoxy LXXIII-2504-methoxycinnamyl methoxy LXXIII-251 4-ethoxycinnamyl methoxy LXXIII-2524-cyanocinnamyl methoxy LXXIII-253 3-(6-chloro-pyridin-3-yl)-allylmethoxy LXXIII-254 3-(4-chlorophenyl)-but-2-enyl methoxy LXXIII-2553-(4-chlorophenyl)-3-fluoro-allyl methoxy LXXIII-2563-chloro-4-fluoro-cinnamyl methoxy LXXIII-257 3,5-dichloro-cinnamylmethoxy LXXIII-258 5-phenyl-penta-2,4-dienyl methoxy LXXIII-2594-isopropyloxycarbonylamino-cinnamyl methoxy LXXIII-2603-naphthalen-2-yl-allyl methoxy LXXIII-2613-(5-trifluoromethyl-pyridin-2-yl)-allyl methoxy LXXIII-2623-(5-chloro-pyridin-2-yl)-allyl methoxy LXXIII-263 3-pyridin-4-yl-allylmethoxy LXXIII-264 3-(2-Chloro-pyridin-4-yl)-allyl methoxy LXXIII-265Cinnamyl 2,1,3-benzoxadiazole-5-yl LXXIII-266 4-chlorocinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-267 4-fluorocinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-268 4-bromocinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-269 4-trifluoromethylcinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-270 4-trifluoromethoxycinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-271 4-pentafluoroethoxycinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-272 4-methoxycinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-273 4-ethoxycinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-274 4-cyanocinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-275 3-(6-chloro-pyridin-3-yl)-allyl2,1,3-benzoxadiazole-5-yl LXXIII-276 3-(4-chlorophenyl)-but-2-enyl2,1,3-benzoxadiazole-5-yl LXXIII-277 3-(4-chlorophenyl)-3-fluoro-allyl2,1,3-benzoxadiazole-5-yl LXXIII-278 3-chloro-4-fluoro-cinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-279 3,5-dichloro-cinnamyl2,1,3-benzoxadiazole-5-yl LXXIII-280 5-phenyl-penta-2,4-dienyl2,1,3-benzoxadiazole-5-yl LXXIII-2814-isopropyloxycarbonylamino-cinnamyl 2,1,3-benzoxadiazole-5-ylLXXIII-282 3-naphthalen-2-yl-allyl 2,1,3-benzoxadiazole-5-yl LXXIII-2833-(5-trifluoromethyl-pyridin-2-yl)-allyl 2,1,3-benzoxadiazole-5-ylLXXIII-284 3-(5-chloro-pyridin-2-yl)-allyl 2,1,3-benzoxadiazole-5-ylLXXIII-285 3-pyridin-4-yl-allyl 2,1,3-benzoxadiazole-5-yl LXXIII-2863-(2-Chloro-pyridin-4-yl)-allyl 2,1,3-benzoxadiazole-5-yl LXXIII-287Cinnamyl methoxypropylamino LXXIII-288 4-chlorocinnamylmethoxypropylamino LXXIII-289 4-fluorocinnamyl methoxypropylaminoLXXIII-290 4-bromocinnamyl methoxypropylamino LXXIII-2914-trifluoromethylcinnamyl methoxypropylamino LXXIII-2924-trifluoromethoxycinnamyl methoxypropylamino LXXIII-2934-pentafluoroethoxycinnamyl methoxypropylamino LXXIII-2944-methoxycinnamyl methoxypropylamino LXXIII-295 4-ethoxycinnamylmethoxypropylamino LXXIII-296 4-cyanocinnamyl methoxypropylaminoLXXIII-297 3-(6-chloro-pyridin-3-yl)-allyl methoxypropylamino LXXIII-2983-(4-chlorophenyl)-but-2-enyl methoxypropylamino LXXIII-2993-(4-chlorophenyl)-3-fluoro-allyl methoxypropylamino LXXIII-3003-chloro-4-fluoro-cinnamyl methoxypropylamino LXXIII-3013,5-dichloro-cinnamyl methoxypropylamino LXXIII-3025-phenyl-penta-2,4-dienyl methoxypropylamino LXXIII-3034-isopropyloxycarbonylamino-cinnamyl methoxypropylamino LXXIII-3043-naphthalen-2-yl-allyl methoxypropylamino LXXIII-3053-(5-trifluoromethyl-pyridin-2-yl)-allyl methoxypropylamino LXXIII-3063-(5-chloro-pyridin-2-yl)-allyl methoxypropylamino LXXIII-3073-pyridin-4-yl-allyl methoxypropylamino LXXIII-3083-(2-Chloro-pyridin-4-yl)-allyl methoxypropylamino LXXIII-309 Cinnamyl2-chloro-thiazol-5-yl LXXIII-310 4-chlorocinnamyl 2-chloro-thiazol-5-ylLXXIII-311 4-fluorocinnamyl 2-chloro-thiazol-5-yl LXXIII-3124-bromocinnamyl 2-chloro-thiazol-5-yl LXXIII-3134-trifluoromethylcinnamyl 2-chloro-thiazol-5-yl LXXIII-3144-trifluoromethoxycinnamyl 2-chloro-thiazol-5-yl LXXIII-3154-pentafluoroethoxycinnamyl 2-chloro-thiazol-5-yl LXXIII-3164-methoxycinnamyl 2-chloro-thiazol-5-yl LXXIII-317 4-ethoxycinnamyl2-chloro-thiazol-5-yl LXXIII-318 4-cyanocinnamyl 2-chloro-thiazol-5-ylLXXIII-319 3-(6-chloro-pyridin-3-yl)-allyl 2-chloro-thiazol-5-ylLXXIII-320 3-(4-chlorophenyl)-but-2-enyl 2-chloro-thiazol-5-ylLXXIII-321 3-(4-chlorophenyl)-3-fluoro-allyl 2-chloro-thiazol-5-ylLXXIII-322 3-chloro-4-fluoro-cinnamyl 2-chloro-thiazol-5-yl LXXIII-3233,5-dichloro-cinnamyl 2-chloro-thiazol-5-yl LXXIII-3245-phenyl-penta-2,4-dienyl 2-chloro-thiazol-5-yl LXXIII-3254-isopropyloxycarbonylamino-cinnamyl 2-chloro-thiazol-5-yl LXXIII-3263-naphthalen-2-yl-allyl 2-chloro-thiazol-5-yl LXXIII-3273-(5-trifluoromethyl-pyridin-2-yl)-allyl 2-chloro-thiazol-5-ylLXXIII-328 3-(5-chloro-pyridin-2-yl)-allyl 2-chloro-thiazol-5-ylLXXIII-329 3-pyridin-4-yl-allyl 2-chloro-thiazol-5-yl LXXIII-3303-(2-Chloro-pyridin-4-yl)-allyl 2-chloro-thiazol-5-yl LXXIII-331Cinnamyl i-propylamino LXXIII-332 4-chlorocinnamyl i-propylaminoLXXIII-333 4-fluorocinnamyl i-propylamino LXXIII-334 4-bromocinnamyli-propylamino LXXIII-335 4-trifluoromethylcinnamyl i-propylaminoLXXIII-336 4-trifluoromethoxycinnamyl i-propylamino LXXIII-3374-pentafluoroethoxycinnamyl i-propylamino LXXIII-338 4-methoxycinnamyli-propylamino LXXIII-339 4-ethoxycinnamyl i-propylamino LXXIII-3404-cyanocinnamyl i-propylamino LXXIII-341 3-(6-chloro-pyridin-3-yl)-allyli-propylamino LXXIII-342 3-(4-chlorophenyl)-but-2-enyl i-propylaminoLXXIII-343 3-(4-chlorophenyl)-3-fluoro-allyl i-propylamino LXXIII-3443-chloro-4-fluoro-cinnamyl i-propylamino LXXIII-3453,5-dichloro-cinnamyl i-propylamino LXXIII-346 5-phenyl-penta-2,4-dienyli-propylamino LXXIII-347 4-isopropyloxycarbonylamino-cinnamyli-propylamino LXXIII-348 3-naphthalen-2-yl-allyl i-propylaminoLXXIII-349 3-(5-trifluoromethyl-pyridin-2-yl)-allyl i-propylaminoLXXIII-350 3-(5-chloro-pyridin-2-yl)-allyl i-propylamino LXXIII-3513-pyridin-4-yl-allyl i-propylamino LXXIII-3523-(2-Chloro-pyridin-4-yl)-allyl i-propylamino LXXIII-353 Cinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-354 4-chlorocinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-355 4-fluorocinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-356 4-bromocinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-357 4-trifluoromethylcinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-358 4-trifluoromethoxycinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-359 4-pentafluoroethoxycinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-360 4-methoxycinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-361 4-ethoxycinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-362 4-cyanocinnamyl1,3-dioxolan-2-yl-ethylamino LXXIII-363 3-(6-chloro-pyridin-3-yl)-allyl1,3-dioxolan-2-yl-ethylamino LXXIII-364 3-(4-chlorophenyl)-but-2-enyl1,3-dioxolan-2-yl-ethylamino LXXIII-3653-(4-chlorophenyl)-3-fluoro-allyl 1,3-dioxolan-2-yl-ethylaminoLXXIII-366 3-chloro-4-fluoro-cinnamyl 1,3-dioxolan-2-yl-ethylaminoLXXIII-367 3,5-dichloro-cinnamyl 1,3-dioxolan-2-yl-ethylamino LXXIII-3685-phenyl-penta-2,4-dienyl 1,3-dioxolan-2-yl-ethylamino LXXIII-3694-isopropyloxycarbonylamino-cinnamyl 1,3-dioxolan-2-yl-ethylaminoLXXIII-370 3-naphthalen-2-yl-allyl 1,3-dioxolan-2-yl-ethylaminoLXXIII-371 3-(5-trifluoromethyl-pyridin-2-yl)-allyl1,3-dioxolan-2-yl-ethylamino LXXIII-372 3-(5-chloro-pyridin-2-yl)-allyl1,3-dioxolan-2-yl-ethylamino LXXIII-373 3-pyridin-4-yl-allyl1,3-dioxolan-2-yl-ethylamino LXXIII-374 3-(2-Chloro-pyridin-4-yl)-allyl1,3-dioxolan-2-yl-ethylamino LXXIII-375 Cinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-376 4-chlorocinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-377 4-fluorocinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-378 4-bromocinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-379 4-trifluoromethylcinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-380 4-trifluoromethoxycinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-381 4-pentafluoroethoxycinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-382 4-methoxycinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-383 4-ethoxycinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-384 4-cyanocinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-3853-(6-chloro-pyridin-3-yl)-allyl 2-chloro-pyrid-4-yl-methylaminoLXXIII-386 3-(4-chlorophenyl)-but-2-enyl 2-chloro-pyrid-4-yl-methylaminoLXXIII-387 3-(4-chlorophenyl)-3-fluoro-allyl2-chloro-pyrid-4-yl-methylamino LXXIII-388 3-chloro-4-fluoro-cinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-389 3,5-dichloro-cinnamyl2-chloro-pyrid-4-yl-methylamino LXXIII-390 5-phenyl-penta-2,4-dienyl2-chloro-pyrid-4-yl-methylamino LXXIII-3914-isopropyloxycarbonylamino-cinnamyl 2-chloro-pyrid-4-yl-methylaminoLXXIII-392 3-naphthalen-2-yl-allyl 2-chloro-pyrid-4-yl-methylaminoLXXIII-393 3-(5-trifluoromethyl-pyridin-2-yl)-allyl2-chloro-pyrid-4-yl-methylamino LXXIII-3943-(5-chloro-pyridin-2-yl)-allyl 2-chloro-pyrid-4-yl-methylaminoLXXIII-395 3-pyridin-4-yl-allyl 2-chloro-pyrid-4-yl-methylaminoLXXIII-396 3-(2-Chloro-pyridin-4-yl)-allyl2-chloro-pyrid-4-yl-methylamino LXXIII-397 Cinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-398 4-chlorocinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-399 4-fluorocinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-400 4-bromocinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-4014-trifluoromethylcinnamyl 2-trfluoromethyl-pyrid-5-yl- methylaminoLXXIII-402 4-trifluoromethoxycinnamyl 2-trfluoromethyl-pyrid-5-yl-methylamino LXXIII-403 4-pentafluoroethoxycinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-404 4-methoxycinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-405 4-ethoxycinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-406 4-cyanocinnamyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-4073-(6-chloro-pyridin-3-yl)-allyl 2-trfluoromethyl-pyrid-5-yl- methylaminoLXXIII-408 3-(4-chlorophenyl)-but-2-enyl 2-trfluoromethyl-pyrid-5-yl-methylamino LXXIII-409 3-(4-chlorophenyl)-3-fluoro-allyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-4103-chloro-4-fluoro-cinnamyl 2-trfluoromethyl-pyrid-5-yl- methylaminoLXXIII-411 3,5-dichloro-cinnamyl 2-trfluoromethyl-pyrid-5-yl-methylamino LXXIII-412 5-phenyl-penta-2,4-dienyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-4134-isopropyloxycarbonylamino-cinnamyl 2-trfluoromethyl-pyrid-5-yl-methylamino LXXIII-414 3-naphthalen-2-yl-allyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-4153-(5-trifluoromethyl-pyridin-2-yl)-allyl 2-trfluoromethyl-pyrid-5-yl-methylamino LXXIII-416 3-(5-chloro-pyridin-2-yl)-allyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-417 3-pyridin-4-yl-allyl2-trfluoromethyl-pyrid-5-yl- methylamino LXXIII-4183-(2-Chloro-pyridin-4-yl)-allyl 2-trfluoromethyl-pyrid-5-yl- methylaminoLXXIII-419 Cinnamyl methylamino LXXIII-420 4-chlorocinnamyl methylaminoLXXIII-421 4-fluorocinnamyl methylamino LXXIII-422 4-bromocinnamylmethylamino LXXIII-423 4-trifluoromethylcinnamyl methylamino LXXIII-4244-trifluoromethoxycinnamyl methylamino LXXIII-4254-pentafluoroethoxycinnamyl methylamino LXXIII-426 4-methoxycinnamylmethylamino LXXIII-427 4-ethoxycinnamyl methylamino LXXIII-4284-cyanocinnamyl methylamino LXXIII-429 3-(6-chloro-pyridin-3-yl)-allylmethylamino LXXIII-430 3-(4-chlorophenyl)-but-2-enyl methylaminoLXXIII-431 3-(4-chlorophenyl)-3-fluoro-allyl methylamino LXXIII-4323-chloro-4-fluoro-cinnamyl methylamino LXXIII-433 3,5-dichloro-cinnamylmethylamino LXXIII-434 5-phenyl-penta-2,4-dienyl methylamino LXXIII-4354-isopropyloxycarbonylamino-cinnamyl methylamino LXXIII-4363-naphthalen-2-yl-allyl methylamino LXXIII-4373-(5-trifluoromethyl-pyridin-2-yl)-allyl methylamino LXXIII-4383-(5-chloro-pyridin-2-yl)-allyl methylamino LXXIII-4393-pyridin-4-yl-allyl methylamino LXXIII-4403-(2-Chloro-pyridin-4-yl)-allyl methylamino LXXIII-441 Cinnamylethylamino LXXIII-442 4-chlorocinnamyl ethylamino LXXIII-4434-fluorocinnamyl ethylamino LXXIII-444 4-bromocinnamyl ethylaminoLXXIII-445 4-trifluoromethylcinnamyl ethylamino LXXIII-4464-trifluoromethoxycinnamyl ethylamino LXXIII-4474-pentafluoroethoxycinnamyl ethylamino LXXIII-448 4-methoxycinnamylethylamino LXXIII-449 4-ethoxycinnamyl ethylamino LXXIII-4504-cyanocinnamyl ethylamino LXXIII-451 3-(6-chloro-pyridin-3-yl)-allylethylamino LXXIII-452 3-(4-chlorophenyl)-but-2-enyl ethylaminoLXXIII-453 3-(4-chlorophenyl)-3-fluoro-allyl ethylamino LXXIII-4543-chloro-4-fluoro-cinnamyl ethylamino LXXIII-455 3,5-dichloro-cinnamylethylamino LXXIII-456 5-phenyl-penta-2,4-dienyl ethylamino LXXIII-4574-isopropyloxycarbonylamino-cinnamyl ethylamino LXXIII-4583-naphthalen-2-yl-allyl ethylamino LXXIII-4593-(5-trifluoromethyl-pyridin-2-yl)-allyl ethylamino LXXIII-4603-(5-chloro-pyridin-2-yl)-allyl ethylamino LXXIII-4613-pyridin-4-yl-allyl ethylamino LXXIII-4623-(2-Chloro-pyridin-4-yl)-allyl ethylamino LXXIII-463 Cinnamyl2-chloro-pyrid-4-yl-amino LXXIII-464 4-chlorocinnamyl2-chloro-pyrid-4-yl-amino LXXIII-465 4-fluorocinnamyl2-chloro-pyrid-4-yl-amino LXXIII-466 4-bromocinnamyl2-chloro-pyrid-4-yl-amino LXXIII-467 4-trifluoromethylcinnamyl2-chloro-pyrid-4-yl-amino LXXIII-468 4-trifluoromethoxycinnamyl2-chloro-pyrid-4-yl-amino LXXIII-469 4-pentafluoroethoxycinnamyl2-chloro-pyrid-4-yl-amino LXXIII-470 4-methoxycinnamyl2-chloro-pyrid-4-yl-amino LXXIII-471 4-ethoxycinnamyl2-chloro-pyrid-4-yl-amino LXXIII-472 4-cyanocinnamyl2-chloro-pyrid-4-yl-amino LXXIII-473 3-(6-chloro-pyridin-3-yl)-allyl2-chloro-pyrid-4-yl-amino LXXIII-474 3-(4-chlorophenyl)-but-2-enyl2-chloro-pyrid-4-yl-amino LXXIII-475 3-(4-chlorophenyl)-3-fluoro-allyl2-chloro-pyrid-4-yl-amino LXXIII-476 3-chloro-4-fluoro-cinnamyl2-chloro-pyrid-4-yl-amino LXXIII-477 3,5-dichloro-cinnamyl2-chloro-pyrid-4-yl-amino LXXIII-478 5-phenyl-penta-2,4-dienyl2-chloro-pyrid-4-yl-amino LXXIII-4794-isopropyloxycarbonylamino-cinnamyl 2-chloro-pyrid-4-yl-aminoLXXIII-480 3-naphthalen-2-yl-allyl 2-chloro-pyrid-4-yl-amino LXXIII-4813-(5-trifluoromethyl-pyridin-2-yl)-allyl 2-chloro-pyrid-4-yl-aminoLXXIII-482 3-(5-chloro-pyridin-2-yl)-allyl 2-chloro-pyrid-4-yl-aminoLXXIII-483 3-pyridin-4-yl-allyl 2-chloro-pyrid-4-yl-amino LXXIII-4843-(2-Chloro-pyridin-4-yl)-allyl 2-chloro-pyrid-4-yl-amino LXXIII-485Cinnamyl methoxyethylamino LXXIII-486 4-chlorocinnamyl methoxyethylaminoLXXIII-487 4-fluorocinnamyl methoxyethylamino LXXIII-488 4-bromocinnamylmethoxyethylamino LXXIII-489 4-trifluoromethylcinnamyl methoxyethylaminoLXXIII-490 4-trifluoromethoxycinnamyl methoxyethylamino LXXIII-4914-pentafluoroethoxycinnamyl methoxyethylamino LXXIII-4924-methoxycinnamyl methoxyethylamino LXXIII-493 4-ethoxycinnamylmethoxyethylamino LXXIII-494 4-cyanocinnamyl methoxyethylaminoLXXIII-495 3-(6-chloro-pyridin-3-yl)-allyl methoxyethylamino LXXIII-4963-(4-chlorophenyl)-but-2-enyl methoxyethylamino LXXIII-4973-(4-chlorophenyl)-3-fluoro-allyl methoxyethylamino LXXIII-4983-chloro-4-fluoro-cinnamyl methoxyethylamino LXXIII-4993,5-dichloro-cinnamyl methoxyethylamino LXXIII-5005-phenyl-penta-2,4-dienyl methoxyethylamino LXXIII-5014-isopropyloxycarbonylamino-cinnamyl methoxyethylamino LXXIII-5023-naphthalen-2-yl-allyl methoxyethylamino LXXIII-5033-(5-trifluoromethyl-pyridin-2-yl)-allyl methoxyethylamino LXXIII-5043-(5-chloro-pyridin-2-yl)-allyl methoxyethylamino LXXIII-5053-pyridin-4-yl-allyl methoxyethylamino LXXIII-5063-(2-Chloro-pyridin-4-yl)-allyl methoxyethylaminoTable LXXIV provides 506 compounds of formula Iya

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXV provides 506 compounds of formula Iyb

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXVI provides 506 compounds of formula Iyc

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXVII provides 506 compounds of formula Iyd

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXVIII provides 506 compounds of formula Iye

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXIX provides 506 compounds of formula Iyf

wherein the values of R⁸ and R¹ are given in Table 73.Table LXXX provides 506 compounds of formula Iyg

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXI provides 506 compounds of formula Iyh

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXII provides 506 compounds of formula Iyi

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXIII provides 506 compounds of formula Iyj

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXIV provides 506 compounds of formula Iyk

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXV provides 506 compounds of formula Iyl

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXVI provides 506 compounds of formula Iym

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXVII provides 506 compounds of formula Iyn

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXVIII provides 506 compounds of formula Iyo

wherein the values of R⁸ and R¹ are given in Table 73.

Table LXXXIX provides 506 compounds of formula Iyp

wherein the values of R⁸ and R¹ are given in Table 73.

Table XC provides 506 compounds of formula Iyq

wherein the values of R⁸ and R¹ are given in Table 73.Table XCI provides 506 compounds of formula Iyr

wherein the values of R⁸ and R¹ are given in Table 73.

Table XCII provides 506 compounds of formula Iys

wherein the values of R⁸ and R¹ are given in Table 73.

Table XCIII provides 506 compounds of formula Iyt

wherein the values of R⁸ and R¹ are given in Table 73.

Table XCIV provides 506 compounds of formula Iyu

wherein the values of R⁸ and R¹ are given in Table 73.

Table XCV provides 506 compounds of formula Iyv

wherein the values of R⁸ and R¹ are given in Table 73.

The compounds of the invention may be made by a variety of methods.

For example tetrahydropyridyl compounds of the general formula 1 may beprepared according to the reactions of Scheme 1.

P1 is R⁸ or is a suitable protective group for example a group such asBOC, benzyl or alkyl and S₁ is the group (R⁴)_(n).

The synthetic route shown in Scheme 1 may also be used for thepreparation of some compounds of formula I wherein the ring

is a 5 or 6 membered heteroaromatic ring instead of the phenyl group.

Thus a compound of formula 1 may be obtained from a compound of formula2 by reaction with a suitable electrophilic species. Compounds offormula 1 where Y is a carbonyl group may be formed by the reaction ofcompounds of formula 2 with a carboxylic acid derivative of formulaR¹—C(O)—Z′ where Z′ is chloride, hydroxy, alkoxy or acyloxy at atemperature between 0° C. and 150° C. optionally in an organic solventsuch as dichloromethane, chloroform or 1,2-dichloroethane, optionally inthe presence of a tertiary amine base such as triethylamine ordiisopropylethylamine and optionally in the presence of a coupling agentsuch as dicyclohexylcarbodiimide. Compounds of formula 1 where Y is acarbonyl group and R¹ is an amino substituent of formula R′—NH— may beformed by the reaction of compounds of formula 2 with an isocyanate offormula R′—N═C═O under similar conditions. Compounds of formula 1 whereY is a group of formula S(O)_(m) may be formed from compounds of formula2 by treatment with compounds of formula of R¹—S(O)_(m)—Cl under similarconditions. Compounds of formula 1 where Y is a thiocarbonyl group andR¹ is an amino substituent of formula R′—NH— may be formed by thereaction of compounds of formula 2 with an isothiocyanate of formulaR′—N═C═S under similar conditions.

Alternatively compounds of formula 1 where Y is a thiocarbonyl group andR¹ is a carbon substituent may be formed by treatment of compounds offormula 1 where Y is a carbonyl group and R¹ is a carbon substituentwith a suitable thionating agent such as Lawesson's reagent.

In the above procedures, acid derivatives of the formula R¹—C(O)—Z′,isocyanates of formula R′—N═C═O, isothiocyanates of formula R′—N═C═S andsulfur electrophiles of formula R¹—S(O)_(m)—Cl are either knowncompounds or may be formed from known compounds by known methods by aperson skilled in the art.

Compounds of formula 2 may be prepared from compounds of formula 3 bycleavage of the amide bond, according to known methods by a personskilled in the art.

Alternatively compounds of formula 2 may be prepared from compounds offormula 5 where P1 is R⁸ by cleavage of the amide bond, according toknown methods by a person skilled in the art.

Compounds of formula 3 may be obtained from compounds of formula 4 byreaction with an alkylating agent of the formula R⁸-L, where L ischloride, bromide, iodide or a sulfonate (e.g. mesylate or tosylate) orsimilar leaving group at a temperature of between ambient temperatureand 100° C., typically 65° C., in an organic solvent such asdichloromethane, chloroform or 1,2-dichloroethane in the presence of atertiary amine base such as triethylamine or diisopropylethylamine andoptionally catalysed by halide salts such as sodium iodide, potassiumiodide or tetrabutylammonium iodide. Alternatively, a compound offormula 4 may be reacted with an aldehyde of the formula R⁸—CHO at atemperature between ambient temperature and 100° C. in an organicsolvent such as tetrahydrofuran or ethanol or mixtures of solvents inthe presence of a reducing agent such as borane-pyridine complex, sodiumborohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride orsuch like, to produce a compound of formula 3 where R⁸ is CH₂—R.

Compounds of formula 4 may be prepared from compounds of formula 5 whereP1 is benzyl or alkyl by a dealkylation reaction, according to knownmethods by a person skilled in the art. Compounds of formula 4 may beprepared from compounds of formula 5 where P1 is BOC by treatment withan acid such as CF₃COOH, according to known methods by a person skilledin the art.

Alternatively, compounds of formula 4 may be formed by the reaction ofcompounds of formula 6 where P1 is BOC by treatment with HCl or H₂SO₄ inAcOH at a temperature between 0° C. and 150° C. optionally in an inertorganic solvent.

Compounds of formula 5 may be prepared from compounds of formula 6 whereP1 is benzyl or alkyl by a H₂O elimination reaction, according to knownmethods by a person skilled in the art. Most favourable is the treatmentof a compound of formula 6 with conc. HCl or H₂SO₄ in AcOH at atemperature between 0° C. and 150° C.

Alternatively, compounds of formula 5 may be prepared from compounds offormula 6 by treatment with SOCl₂, according to known methods by aperson skilled in the art.

Alternatively, compounds of formula 5 may be formed by the reaction ofcompounds of formula 9 with a carboxylic acid derivative of formulat-Bu-C(O)—Z″ where Z″ is chloride, hydroxy, alkoxy or acyloxy at atemperature between 0° C. and 150° C. optionally in an inert organicsolvent.

Compounds of formula 6 may be prepared from compounds of formula 7 bytreatment of lithiated compounds of formula 7 with a piperidinone at atemperature between −100° C. and 0° C. optionally in an inert organicsolvent, according to known methods by a person skilled in the art.

Compounds of formula 7 and formula 8 are known or may be made from knowncompounds by known methods.

Alternatively compounds of formula 1 may be formed by alkylation ofcompounds of formula 11 as described above for compounds of formula 3.

Compounds of formula 11 may be prepared from compounds of formula 10where P1 is benzyl or alkyl by a dealkylation reaction, according toknown methods by a person skilled in the art.

Compounds of formula 10 may be prepared from compounds of formula 9 bymethods described above for the conversion of compounds of formula 2 tocompounds of formula 1.

Compounds of formula 9 may be prepared from compounds of formula 6 by aH₂O elimination reaction, according to known methods by a person skilledin the art. Most favourable is the treatment of a compound of formula 6with aqueous HCl or H₂SO₄ in AcOH at a temperature between 0° C. and150° C. or with a base in H₂O and an appropriate solvent.

Certain compounds of formula 2, formula 3, formula 4, formula 5, formula6, formula 9, formula 10 and formula 11 are novel and as such form afurther aspect of the invention.

4-Hydroxy-piperidinyl compounds of the general formula 1 may be preparedaccording to the reactions of Scheme 2 using synthetic methodologiesknown by a person skilled in the art and as described above.

P1 is R⁸ or is a suitable protective group for example a group such asBOC, benzyl or alkyl and S₁ is the group (R⁴)_(n).

The synthetic route shown in Scheme 2 may also be used for thepreparation of some compounds of formula I wherein the ring

is a 5 or 6 membered heteroaromatic ring instead of the phenyl group.

Certain compounds of formula 12, formula 13, formula 14, formula 15,formula 16, and formula 17 are novel and as such form a further aspectof the invention.

Piperidinyl compounds of the general formula 1 may be prepared accordingto the reactions of Scheme 3 using synthetic methodologies known by aperson skilled in the art and as described above.

P1 is R⁸ or is a suitable protective group for example a group such asBOC, benzyl or alkyl and S₁ is the group (R⁴)_(n).

The synthetic route shown in Scheme 3 may also be used for thepreparation of some in compounds of formula I wherein the ring

is a 5 or 6 membered heteroaromatic ring instead of the phenyl group.

Certain compounds of formula 18, formula 19, formula 20, formula 21,formula 22, formula 23 and formula 24 are novel and as such form afurther aspect of the invention.

Compounds where the ring

is a 5 or 6 membered heteroaromatic ring instead of the phenyl group canbe prepared by synthetic routes shown in Scheme 1-3 or many other routesand methods known to a person skilled in the art. For example2H-pyrazol-3-yl derivatives can be prepared as shown in Scheme 4.

Certain compounds of formula 25 are novel and as such form a furtheraspect of the invention.

The skilled person will readily recognise that it is possible to convertone compound of formula 1 wherein R² is H or an intermediate of Schemes1-4 to other compounds of formula I or intermediates thereof. Examplesof such transformations are given in Schemes 5, 6 and 7 in which the Rgroups have the meanings as defined for a compound of formula I

Alternatively piperidinyl-aniline derivatives of the general formula 1may be prepared according to the reactions of Schemes 8-13 where S isthe group (On using synthetic methodologies known by a person skilled inthe art and as described above.

A key step in these synthetic routes is a Suzuki coupling reaction toprepare tetrahydropyridin-4-yl-aniline derivatives. Other cross couplingreactions, such as Stille and Negishi couplings, may be applied as well.The boronate reagents may be prepared as described in the literature;for example P. R Eastwood, THL 41, 3705 (2000). Examples of couplingreactions are given in Examples 21-23 which describe the synthesis ofthe compounds in Tables EX23.1-EX23.11.

Instead of the BOC group other suitable protective groups may be used.

The synthetic routes shown in Scheme 8-13 may also be used for thepreparation of compounds of formula I wherein the ring

is a 5 or 6 membered heteroaromatic ring instead of the phenyl group.

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which termincludes the growing of crops for food and fibre products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies).

Examples of pest species which may be controlled by the compounds offormula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid),Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids),Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper),Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp.(stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips),Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis(boll weevil), Aonidiella spp. (scale insects), Trialeurodes spp. (whiteflies), Bemisia tabaci (white fly), Ostrinia nubilalis (European cornborer), Spodoptera littoralis (cotton leafworm), Heliothis virescens(tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpazea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pierisbrassicae (white butterfly), Plutella xylostella (diamond back moth),Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locustamigratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp.(rootworms), Panonychus ulmi (European red mite), Panonychus citri(citrus red mite), Tetranychus urticae (two-spotted spider mite),Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora(citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpusspp. (flat mites), Boophilus microplus (cattle tick), Dermacentorvariabilis (American dog tick), Ctenocephalides felis (cat flea),Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti(mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes),Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplanetaamericana (cockroach), Blatta orientalis (cockroach), termites of theMastotermitidae (for example Mastotermes spp.), the Kalotermitidae (forexample Neotermes spp.), the Rhinotermitidae (for example Coptotermesformosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R.hesperus, and R. santonensis) and the Termitidae (for exampleGlobitermes sulphureus), Solenopsis geminata (fire ant), Monomoriumpharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (bitingand sucking lice), Meloidogyne spp. (root knot nematodes), Globoderaspp. and Heterodera spp. (cyst nematodes), Pratylenchus spp. (lesionnematodes), Rhodopholus spp. (banana burrowing nematodes), Tylenchulusspp. (citrus nematodes), Haemonchus contortus (barber pole worm),Caenorhabditis elegans (vinegar eelworm), Trichostrongylus spp. (gastrointestinal nematodes) and Deroceras reticulatum (slug).

The invention therefore provides a method of combating and controllinginsects, acarines, nematodes or molluscs which comprises applying aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I), or a composition containing acompound of formula (I), to a pest, a locus of pest, or to a plantsusceptible to attack by a pest, The compounds of formula (I) arepreferably used against insects, acarines or nematodes.

The term “plant” as used herein includes seedlings, bushes and trees.

In order to apply a compound of formula (I) as an insecticide,acaricide, nematicide or molluscicide to a pest, a locus of pest, or toa plant susceptible to attack by a pest, a compound of formula (I) isusually formulated into a composition which includes, in addition to thecompound of formula (I), a suitable inert diluent or carrier and,optionally, a surface active agent (SFA). SFAs are chemicals which areable to modify the properties of an interface (for example,liquid/solid, liquid/air or liquid/liquid interfaces) by lowering theinterfacial tension and thereby leading to changes in other properties(for example dispersion, emulsification and wetting). It is preferredthat all compositions (both solid and liquid formulations) comprise, byweight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%,of a compound of formula (I). The composition is generally used for thecontrol of pests such that a compound of formula (I) is applied at arate of from 0.1 g to 10 kg per hectare, preferably from 1 g to 6 kg perhectare, more preferably from 1 g to 1 kg per hectare.

When used in a seed dressing, a compound of formula (I) is used at arate of 0.0001 g to 10 g (for example 0.001 g or 0.05 g), preferably0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogram of seed.

In another aspect the present invention provides an insecticidal,acaricidal, nematicidal or molluscicidal composition comprising aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I) and a suitable carrier or diluenttherefor. The composition is preferably an insecticidal, acaricidal,nematicidal or molluscicidal composition.

In a still further aspect the invention provides a method of combatingand controlling pests at a locus which comprises treating the pests orthe locus of the pests with an insecticidally, acaricidally,nematicidally or molluscicidally effective amount of a compositioncomprising a compound of formula (I). The compounds of formula (I) arepreferably used against insects, acarines or nematodes.

The compositions can be chosen from a number of formulation types,including dustable powders (DP), soluble powders (SP), water solublegranules (SG), water dispersible granules (WG), wettable powders (WP),granules (GR) (slow or fast release), soluble concentrates (SL), oilmiscible liquids (OL), ultra low volume liquids (UL), emulsifiableconcentrates (EC), dispersible concentrates (DC), emulsions (both oil inwater (EW) and water in oil (EO)), micro-emulsions (ME), suspensionconcentrates (SC), aerosols, fogging/smoke formulations, capsulesuspensions (CS) and seed treatment formulations. The formulation typechosen in any instance will depend upon the particular purpose envisagedand the physical, chemical and biological properties of the compound offormula (I).

Dustable powders (DP) may be prepared by mixing a compound of formula(I) with one or more solid diluents (for example natural clays, kaolin,pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk,diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulphur, lime, flours, talc and other organic and inorganicsolid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (I)with one or more water-soluble inorganic salts (such as sodiumbicarbonate, sodium carbonate or magnesium sulphate) or one or morewater-soluble organic solids (such as a polysaccharide) and, optionally,one or more wetting agents, one or more dispersing agents or a mixtureof said agents to improve water dispersibility/solubility. The mixtureis then ground to a fine powder. Similar compositions may also begranulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula(I) with one or more solid diluents or carriers, one or more wettingagents and, preferably, one or more dispersing agents and, optionally,one or more suspending agents to facilitate the dispersion in liquids.The mixture is then ground to a fine powder. Similar compositions mayalso be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of acompound of formula (I) and one or more powdered solid diluents orcarriers, or from pre-formed blank granules by absorbing a compound offormula (I) (or a solution thereof, in a suitable agent) in a porousgranular material (such as pumice, attapulgite clays, fuller's earth,kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing acompound of formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates,sulphates or phosphates) and drying if necessary. Agents which arecommonly used to aid absorption or adsorption include solvents (such asaliphatic and aromatic petroleum solvents, alcohols, ethers, ketones andesters) and sticking agents (such as polyvinyl acetates, polyvinylalcohols, dextrins, sugars and vegetable oils). One or more otheradditives may also be included in granules (for example an emulsifyingagent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compoundof formula (I) in water or an organic solvent, such as a ketone, alcoholor glycol ether. These solutions may contain a surface active agent (forexample to improve water dilution or prevent crystallisation in a spraytank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may beprepared by dissolving a compound of formula (I) in an organic solvent(optionally containing one or more wetting agents, one or moreemulsifying agents or a mixture of said agents). Suitable organicsolvents for use in ECs include aromatic hydrocarbons (such asalkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100,SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark),ketones (such as cyclohexanone or methylcyclohexanone) and alcohols(such as benzyl alcohol, furfuryl alcohol or butanol),N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone),dimethyl amides of fatty acids (such as C₈-C₁₀ fatty acid dimethylamide)and chlorinated hydrocarbons. An EC product may spontaneously emulsifyon addition to water, to produce an emulsion with sufficient stabilityto allow spray application through appropriate equipment. Preparation ofan EW involves obtaining a compound of formula (I) either as a liquid(if it is not a liquid at room temperature, it may be melted at areasonable temperature, typically below 70° C.) or in solution (bydissolving it in an appropriate solvent) and then emulsifiying theresultant liquid or solution into water containing one or more SFAs,under high shear, to produce an emulsion. Suitable solvents for use inEWs include vegetable oils, chlorinated hydrocarbons (such aschlorobenzenes), aromatic solvents (such as alkylbenzenes oralkylnaphthalenes) and other appropriate organic solvents which have alow solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of oneor more solvents with one or more SFAs, to produce spontaneously athermodynamically stable isotropic liquid formulation. A compound offormula (I) is present initially in either the water or the solvent/SFAblend. Suitable solvents for use in MEs include those hereinbeforedescribed for use in in ECs or in EWs. An ME may be either anoil-in-water or a water-in-oil system (which system is present may bedetermined by conductivity measurements) and may be suitable for mixingwater-soluble and oil-soluble pesticides in the same formulation. An MEis suitable for dilution into water, either remaining as a microemulsionor forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueoussuspensions of finely divided insoluble solid particles of a compound offormula (I). SCs may be prepared by ball or bead milling the solidcompound of formula (I) in a suitable medium, optionally with one ormore dispersing agents, to produce a fine particle suspension of thecompound. One or more wetting agents may be included in the compositionand a suspending agent may be included to reduce the rate at which theparticles settle. Alternatively, a compound of formula (I) may be drymilled and added to water, containing agents hereinbefore described, toproduce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitablepropellant (for example n-butane). A compound of formula (I) may also bedissolved or dispersed in a suitable medium (for example water or awater miscible liquid, such as n-propanol) to provide compositions foruse in non-pressurised, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with apyrotechnic mixture to form a composition suitable for generating, in anenclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to thepreparation of EW formulations but with an additional polymerisationstage such that an aqueous dispersion of oil droplets is obtained, inwhich each oil droplet is encapsulated by a polymeric shell and containsa compound of formula (I) and, optionally, a carrier or diluenttherefor. The polymeric shell may be produced by either an interfacialpolycondensation reaction or by a coacervation procedure. Thecompositions may provide for controlled release of the compound offormula (I) and they may be used for seed treatment. A compound offormula (I) may also be formulated in a biodegradable polymeric matrixto provide a slow, controlled release of the compound.

A composition may include one or more additives to improve thebiological performance of the composition (for example by improvingwetting, retention or distribution on surfaces; resistance to rain ontreated surfaces; or uptake or mobility of a compound of formula (I)).Such additives include surface active agents, spray additives based onoils, for example certain mineral oils or natural plant oils (such assoy bean and rape seed oil), and blends of these with otherbio-enhancing adjuvants (ingredients which may aid or modify the actionof a compound of formula (I)).

A compound of formula (I) may also be formulated for use as a seedtreatment, for example as a powder composition, including a powder fordry seed treatment (DS), a water soluble powder (SS) or a waterdispersible powder for slurry treatment (WS), or as a liquidcomposition, including a flowable concentrate (FS), a solution (LS) or acapsule suspension (CS). The preparations of DS, SS, WS, FS and LScompositions are very similar to those of, respectively, DP, SP, WP, SCand DC compositions described above. Compositions for treating seed mayinclude an agent for assisting the adhesion of the composition to theseed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surfaceSFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds(for example cetyltrimethyl ammonium bromide), imidazolines and aminesalts.

Suitable anionic SFAs include alkali metals salts of fatty acids, saltsof aliphatic monoesters of sulphuric acid (for example sodium laurylsulphate), salts of sulphonated aromatic compounds (for example sodiumdodecylbenzenesulphonate, calcium dodecylbenzenesulphonate,butylnaphthalene sulphonate and mixtures of sodium di-isopropyl- andtri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ethersulphates (for example sodium laureth-3-sulphate), ether carboxylates(for example sodium laureth-3-carboxylate), phosphate esters (productsfrom the reaction between one or more fatty alcohols and phosphoric acid(predominately mono-esters) or phosphorus pentoxide (predominatelydi-esters), for example the reaction between lauryl alcohol andtetraphosphoric acid; additionally these products may be ethoxylated),sulphosuccinamates, paraffin or olefine sulphonates, taurates andlignosulphonates.

Suitable SFAs of the amphoteric type include betaines, propionates andglycinates.

Suitable SFAs of the non-ionic type include condensation products ofalkylene oxides, such as ethylene oxide, propylene oxide, butylene oxideor mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetylalcohol) or with alkylphenols (such as octylphenol, nonylphenol oroctylcresol); partial esters derived from long chain fatty acids orhexitol anhydrides; condensation products of said partial esters withethylene oxide; block polymers (comprising ethylene oxide and propyleneoxide); alkanolamides; simple esters (for example fatty acidpolyethylene glycol esters); amine oxides (for example lauryl dimethylamine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such aspolysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose)and swelling clays (such as bentonite or attapulgite).

A compound of formula (I) may be applied by any of the known means ofapplying pesticidal compounds. For example, it may be applied,formulated or unformulated, to the pests or to a locus of the pests(such as a habitat of the pests, or a growing plant liable toinfestation by the pests) or to any part of the plant, including thefoliage, stems, branches or roots, to the seed before it is planted orto other media in which plants are growing or are to be planted (such assoil surrounding the roots, the soil generally, paddy water orhydroponic culture systems), directly or it may be sprayed on, dustedon, applied by dipping, applied as a cream or paste formulation, appliedas a vapour or applied through distribution or incorporation of acomposition (such as a granular composition or a composition packed in awater-soluble bag) in soil or an aqueous environment.

A compound of formula (I) may also be injected into plants or sprayedonto vegetation using electrodynamic spraying techniques or other lowvolume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions ordispersions) are generally supplied in the form of a concentratecontaining a high proportion of the active ingredient, the concentratebeing added to water before use. These concentrates, which may includeDCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often requiredto withstand storage for prolonged periods and, after such storage, tobe capable of addition to water to form aqueous preparations whichremain homogeneous for a sufficient time to enable them to be applied byconventional spray equipment. Such aqueous preparations may containvarying amounts of a compound of formula (I) (for example 0.0001 to 10%,by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilisers (forexample nitrogen-, potassium- or phosphorus-containing fertilisers).Suitable formulation types include granules of fertiliser. The mixturessuitably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertiliser compositioncomprising a fertiliser and a compound of formula (I).

The compositions of this invention may contain other compounds havingbiological activity, for example micronutrients or compounds havingfungicidal activity or which possess plant growth regulating,herbicidal, insecticidal, nematicidal or acaricidal activity.

The compound of formula (I) may be the sole active ingredient of thecomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may: provide a composition having a broader spectrum ofactivity or increased persistence at a locus; synergise the activity orcomplement the activity (for example by increasing the speed of effector overcoming repellency) of the compound of formula (I); or help toovercome or prevent the development of resistance to individualcomponents. The particular additional active ingredient will depend uponthe intended utility of the composition. Examples of suitable pesticidesinclude the following:

a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate,esfenvalerate, deltamethrin, cyhalothrin (in particularlambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin,fish safe pyrethroids (for example ethofenprox), natural pyrethrin,tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or5-benzyl-3-furylmethyl-(E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate;b) Organophosphates, such as, profenofos, sulprofos, acephate, methylparathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon,fenamiphos, monocrotophos, profenofos, triazophos, methamidophos,dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos,fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl,pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon;c) Carbamates (including aryl carbamates), such as pirimicarb,triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb,aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur,methomyl or oxamyl;d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron,flufenoxuron or chlorfluazuron;e) Organic tin compounds, such as cyhexatin, fenbutatin oxide orazocyclotin;f) Pyrazoles, such as tebufenpyrad and fenpyroximate;g) Macrolides, such as avermectins or milbemycins, for exampleabamectin, emamectin benzoate, ivermectin, milbemycin, spinosad orazadirachtin;h) Hormones or pheromones;i) Organochlorine compounds such as endosulfan, benzene hexachloride,DDT, chlordane or dieldrin;j) Amidines, such as chlordimeform or amitraz;k) Fumigant agents, such as chloropicrin, dichloropropane, methylbromide or metam;l) Chloronicotinyl compounds such as imidacloprid, thiacloprid,acetamiprid, nitenpyram or thiamethoxam;m) Diacylhydrazines, such as tebufenozide, chromafenozide ormethoxyfenozide;n) Diphenyl ethers, such as diofenolan or pyriproxifen;

o) Indoxacarb; p) Chlorfenapyr; or q) Pymetrozine.

In addition to the major chemical classes of pesticide listed above,other pesticides having particular targets may be employed in thecomposition, if appropriate for the intended utility of the composition.For instance, selective insecticides for particular crops, for examplestemborer specific insecticides (such as cartap) or hopper specificinsecticides (such as buprofezin) for use in rice may be employed.Alternatively insecticides or acaricides specific for particular insectspecies/stages may also be included in the compositions (for exampleacaricidal ovo-larvicides, such as clofentezine, flubenzimine,hexythiazox or tetradifon; acaricidal motilicides, such as dicofol orpropargite; acaricides, such as bromopropylate or chlorobenzilate; orgrowth regulators, such as hydramethylnon, cyromazine, methoprene,chlorfluazuron or diflubenzuron).

Examples of fungicidal compounds which may be included in thecomposition of the invention are(E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide(SSF-129),4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,α-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-γ-butyrolactone,4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916,cyamidazosulfamid),3-5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide(RH-7281, zoxamide),N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide(MON65500),N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide(AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,acibenzolar (CGA245704), alanycarb, aldimorph, anilazine, azaconazole,azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S,bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazimchlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397,chinomethionate, chlorothalonil, chlorozolinate, clozylacon, coppercontaining compounds such as copper oxychloride, copper oxyquinolate,copper sulphate, copper tallate and Bordeaux mixture, cymoxanil,cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulphide1,1′-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb,difenoconazole, difenzoquat, diflumetorim, O,O-di-iso-propyl-5-benzylthiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol,diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride,dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol,ethyl(Z)—N-benzyl-N([methyl(methyl-thioethylideneaminooxycarbonyl)amino]thio)-β-alaninate,etridiazole, famoxadone, fenamidone (RPA407213), fenarimol,fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone,fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole,flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl,furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole,imazalil, imibenconazole, iminoctadine, iminoctadine triacetate,ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanylbutyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054,LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil,metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin,myclobutanil, neoasozin, nickel dimethyldithiocarbamate,nitrothal-isopropyl, nuarimol, ofurace, organomercury compounds,oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin,pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-Al,phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D,polyram, probenazole, prochloraz, procymidone, propamocarb,propiconazole, propineb, propionic acid, pyrazophos, pyrifenox,pyrimethanil, pyroquilon, pyroxyfur, pyrroInitrin, quaternary ammoniumcompounds, quinomethionate, quinoxyfen, quintozene, sipconazole (F-155),sodium pentachlorophenate, spiroxamine, streptomycin, sulphur,tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl,thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon,triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph,trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole,validamycin A, vapam, vinclozolin, zineb and ziram.

The compounds of formula (I) may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The invention is illustrated by the following Examples:

Mass spectra data were obtained for selected compounds of the followingexamples using LCMS: LC5: 254 nm—gradient 10% A to 100% B A=H2O+0.01%HCOOH B=CH3CN/CH3OH+0.01% HCOOH positive electrospray 150-1000 m/z.

EXAMPLE 1

This Example illustrates the preparation ofN-(4-Chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy-piperidin-4-yl}-phenyl)-2,2-dimethyl-propionamide

Step A: Preparation of N-(4-Chloro-phenyl)-2,2-dimethyl-propionamide

To a solution of 4-chloroaniline (25.51 g) and triethylamine (69.73 ml)in chloroform (350 ml) were added 2,2-dimethyl-propionyl chloride (25.32g) over a 30 minutes period. The resulting solution was stirred at r.t.for 1 hour, then water was added and the mixture extracted three timeswith ethyl acetate. The combined organic layers were dried over sodiumsulfate and concentrated in vacuo to afford 35.8 g of product. M.p.149-150° C.; Retention Time HPLC 2.83 min; MS (ES+) 212 (M+H⁺).

Step B: Preparation ofN-(4-Chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy-piperidin-4-yl}-phenyl)-2,2-dimethyl-propionamide

A solution of n-buthyllithium in hexane (47.0 ml of a 1.6 M solution)was added dropwise to a solution ofN-(4-chloro-phenyl)-2,2-dimethyl-propionamide (6.35 g) in dry THF (100ml) at −5° C. under a N₂ atmosphere over 15 min. The resulting solutionwas stirred at 0° C. for 2 hours, and then a solution of1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-one (7.49 g) in THF (15ml) was added dropewise to the above solution of the dianion at 0° C.over a 1 hour period. The reaction mixture was stirred for 2 hours at 0°C. and then overnight at r.t. The solution was then poured into icewater, made acidic with conc. HCl and extracted with ethyl acetate. Thewater layer was made basic and extracted three times with ethyl acetate.The combined organic layers were washed with water, dried over sodiumsulfate and concentrated in vacuo. The residue was subjected to silicagel chromatography (hexane:ethyl acetate:triethyl amine 49:49:2) toafford the title product (6.2 g). M.p. 177-179° C.; Retention Time HPLC2.19 min; MS (ES+) 461 (M+H⁺).

EXAMPLE 2

This Example illustrates the preparation of4-Chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenylamineand4-(2-Amino-5-chloro-phenyl)-1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-ol.

A suspension ofN-(4-chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy-piperidin-4-yl}-phenyl)-2,2-dimethyl-propionamide(1.00 g) in 3N H2SO4 (7.5 ml) and DMSO (3 ml) was heated to refluxtemperature for 48 hours. Then, water was added and the mixtureextracted three times with CH₂Cl₂, the combined organic layers weredried over sodium sulfate and concentrated in vacuo. The residue wassubjected to silica gel chromatography (CH₂Cl₂:MeOH 95:5) to afford4-chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenylamine(0.205 g; viscous oil; Retention Time HPLC 2.15 min; MS (ES+) 359 (M+H⁺)and4-(2-amino-5-chloro-phenyl)-1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-ol(0.182 g; M.p. 168-170° C.; Retention Time HPLC 1.95 min; MS (ES+) 377(M+H⁺).

EXAMPLE 3

This Example illustrates the preparation2-Chloro-N-(4-chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-isonicotinamide

To a solution of 4-chloro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-1,2,3,6tetrahydro-pyridin-4-yl}-phenylamine (60 mg) and triethylamine (0.059ml) in CH₂Cl₂ (10 ml) were added 2-chloro-isonicotinoyl chloride (1.5equivalents; as a 0.2 M solution in CH₂Cl₂) over a 10 minutes period.The resulting solution was stirred at r.t. for 2 hour, poured intosaturated aqueous NaHCO₃ solution and the mixture extracted three timeswith CH₂Cl₂. The combined organic layers were dried over sodium sulfateand concentrated in vacuo. The residue was subjected to silica gelchromatography (hexane:ethyl acetate:triethyl amine 25:73:2) to affordthe title product (28 mg). Viscous oil; Retention Time HPLC 2.28 min; MS(ES+) 500, 498 (M+H⁺).

EXAMPLE 4

This Example illustrates the preparation ofN-[2-(1-Benzyl-4-hydroxy-piperidin-4-yl)-4-chloro-phenyl]-2,2-dimethyl-propionamide

A solution of n-buthyllithium in hexane (22.6 ml of a solutioncontaining 15% n-buthyllithium) was added dropewise to a solution ofN-(4-chloro-phenyl)-2,2-dimethyl-propionamide (3.00 g) in dry THF (80ml) at −5° C. under a N2 atmosphere over 15 min. The resulting solutionwas stirred at 0° C. for 2 hours, and then a solution of1-benzyl-piperidin-4-one (2.67) in THF (4.5 ml) was added dropewise tothe above solution of the dianion at 0° C. over a 1 hour period. Thereaction mixture was stirred for 2 hours at 0° C. and then overnight atr.t. The solution was then poured into ice water, made acidic with conc.HCl and extracted with ethyl acetate. The water layer was made basic andextracted three times with ethyl acetate. The combined organic layerswere washed with water, dried over sodium sulfate and concentrated invacuo. The residue was recrystallized from ethyl acetate/THF to affordthe title product (2.6 g). M.p. 252-255° C.

EXAMPLE 5

This Example illustrates the preparation of2-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenylamine and4-(2-Amino-5-chloro-phenyl)-1-benzyl-piperidin-4-ol.

A suspension ofN-[2-(1-benzyl-4-hydroxy-piperidin-4-yl)-4-chloro-phenyl]-2,2-dimethyl-propionamide(6.00 g) in n-BuOH (50 ml) and 6N HCl (120 ml) was heated to refluxtemperature for 5 days. The solution was then poured into ice water,made acidic with conc. HCl and extracted with ethyl acetate. The waterlayer was made basic and extracted three times with CH₂Cl₂, dried oversodium sulfate and concentrated in vacuo. The residue was subjected tosilica gel chromatography (hexane:ethyl acetate:triethyl amine 49:49:2)to afford2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenylamine (2.11g; viscous oil; Retention Time HPLC 1.81 min; MS (ES+) 299 (M+H⁺)) and4-(2-amino-5-chloro-phenyl)-1-benzyl-piperidin-4-ol (2.11 g; viscousoil; Retention Time HPLC 1.58 min; MS (ES+) 317 (M+H⁺).

EXAMPLE 6

This Example illustrates the preparation ofN-[2-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenyl]-2-chloro-isonicotinamide.

To a solution of2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenylamine (500mg) and triethylamine (0.350 ml) in CHCl₃ (25 ml) were added2-chloro-isonicotinoyl chloride (1.2 equivalents; as a 1.0 M solution inCH₂Cl₂) over a 10 minutes period. The resulting solution was stirred atr.t. overnight, poured into saturated aqueous NaHCO₃ solution and themixture extracted three times with CH₂Cl₂. The combined organic layerswere dried over sodium sulfate and concentrated in vacuo. The residuewas subjected to silica gel chromatography (hexane:ethylacetate:triethyl amine 49:49:2) to afford the title product (595 mg).White solid; Retention Time HPLC 1.89 min; MS (ES+) 440, 438 (M+H⁺).

EXAMPLE 7

This Example illustrates the preparation of2-Chloro-N-[4-chloro-2-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-isonicotinamidehydrochloride.

Step A: Preparation of4-{5-Chloro-2-[(2-chloro-pyridine-4-carbonyl)-amino]phenyl}-3,6-dihydro-2H-pyridine-1-carboxylicacid 1-chloro-ethyl ester

1-Chloroethyl chloroformate (2.64 ml) was added to a suspension ofN-[2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenyl]-2-chloro-isonicotinamide(530 mg) in toluene (30 ml). After 15 min. the solution was heated toreflux for 16 hours, then poured into saturated aqueous NaHCO3 solutionand the mixture extracted three times with CH₂Cl₂. The combined organiclayers were dried over sodium sulfate and concentrated in vacuo toafford the crude title product (550 mg).

Step B: Preparation of2-Chloro-N-[4-chloro-2-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-isonicotinamidehydrochloride

Crude4-{5-chloro-2-[(2-chloro-pyridine-4-carbonyl)-amino]phenyl}-3,6-dihydro-2H-pyridine-1-carboxylicacid 1-chloro-ethyl ester (550 mg) was dissolved in methanol (25 ml) inand heated to reflux for 16 hours. Evaporation afforded the crude titleproduct (465 mg). Retention Time HPLC 1.48 min; MS (ES+) 350, 348(M+H⁺).

EXAMPLE 8

This Example illustrates the preparation of2-Chloro-N-(4-chloro-2-{1-[(E)-3-(4-fluoro-phenyl)-allyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-isonicotinamide

Crude4-{5-chloro-2-[(2-chloro-pyridine-4-carbonyl)-amino]-phenyl}-1-methyl-1,2,3,6-tetrahydro-pyridiniumhydrochloride (69 mg; product obtained in Example 7) was dissolved inacetonitrile (5 ml) and treated with K₂CO₃ (87 mg). Then a solution of1-((E)-3-chloro-propenyl)-4-fluoro-benzene in acetonitrile (1.0 ml) wasadded. After stirring for 3 hours at r.t. and 16 hours at 50° C. andheated to reflux for 16 hours the mixture was filtrated and concentratedin vacuo. The residue was subjected to silica gel chromatography(hexane:ethyl acetate:triethyl amine 74:24:2) to afford the titleproduct (51 mg). Viscous oil; Retention Time HPLC 2.02 min; MS (ES+)484, 482 (M+H⁺).

EXAMPLE 9

This Example illustrates the preparation of2-Chloro-N-(4-chloro-2-{1-[(E)-3-(4-trifluoromethyl-phenyl)-allyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-isonicotinamide

Crude4-{5-chloro-2-[(2-chloro-pyridine-4-carbonyl)-amino]-phenyl}-1-methyl-1,2,3,6-tetrahydro-pyridiniumhydrochloride (69 mg; product obtained in Example 7) was dissolved inacetonitrile (5 ml) and treated with Hünig's base (0.068 ml). Then asolution of 1-((E)-3-chloro-propenyl)-4-trifluoromethyl-benzene (53 mg)in CHCl₃ (1.0 ml) was added. After stirring for 3 hours at r.t. and 16hours at 50° C. and heated to reflux for 16 hours the mixture wasfiltrated and concentrated in vacuo. The residue was subjected to silicagel chromatography (hexane:ethyl acetate:triethyl amine 74:24:2) toafford the title product (23 mg). Viscous oil; Retention Time HPLC 2.02min; MS (ES+) 534, 532 (M+H⁺).

EXAMPLE 10

This Example illustrates the preparation of2-Chloro-N-(4-chloro-2-{1-[(E)-3-(4-trifluoromethoxy-phenyl)-allyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-isonicotinamide

Crude4-{5-chloro-2-[(2-chloro-pyridine-4-carbonyl)-amino]-phenyl}-1-methyl-1,2,3,6-tetrahydro-pyridiniumhydrochloride (69 mg; product obtained in Example 7) was dissolved inacetonitrile (5 ml) and treated with Hünig's base (0.068 ml). Then asolution of 1-((E)-3-chloro-propenyl)-4-trifluoromethoxy-benzene (56 mg)in CHCl₃ (1.0 ml) was added. After stirring for 3 hours at r.t. and 16hours at 50° C. and heated to reflux for 16 hours the mixture wasfiltrated and concentrated in vacuo. The residue was subjected to silicagel chromatography (hexane:ethyl acetate:triethyl amine 74:24:2) toafford the title product (46 mg). Viscous oil; Retention Time HPLC 2.33min; MS (ES+) 550, 548 (M+H⁺).

EXAMPLE 11

This Example illustrates the preparation of2-Chloro-N-{4-chloro-2-[1-((E)-3-phenyl-allyl)1,2,3,6-tetrahydro-pyridin-4-yl]-phenyl}-isonicotinamide

Crude4-{5-chloro-2-[(2-chloro-pyridine-4-carbonyl)-amino]-phenyl}-1-methyl-1,2,3,6-tetrahydro-pyridiniumhydrochloride (69 mg; product obtained in Example 7) was dissolved inacetonitrile (5 ml) and treated with Hünig's base (0.068 ml). Then asolution of ((E)-3-chloro-propenyl)-benzene (32 mg) in CHCl₃ (1.0 ml)was added. After stirring for 3 hours at r.t. and 16 hours at 50° C. andheated to reflux for 16 hours the mixture was filtrated and concentratedin vacuo. The residue was subjected to silica gel chromatography(hexane:ethyl acetate:triethyl amine 74:24:2) to afford the titleproduct (36 mg). Viscous oil; Retention Time HPLC 2.01 min; MS (ES+)466, 464 (M+H⁺).

EXAMPLE 12

This Example illustrates the preparation ofN-[2-(1-Benzyl-4-hydroxy-piperidin-4-yl)-4-fluoro-phenyl]-2,2-dimethyl-propionamide

Step A: Preparation of N-(4-Fluoro-phenyl)-2,2-dimethyl-propionamide

To a solution of 4-fluoroaniline (50.0 g) and triethylamine (157 ml) inCH₂Cl₂ (700 ml) were added 2,2-dimethyl-propionyl chloride (58.0 ml)over a 30 minutes period. The resulting solution was stirred at r.t. for2 hour, then water was added and the mixture extracted three times withethyl acetate. The combined organic layers were dried over sodiumsulfate and concentrated in vacuo to afford 86.0 g of the titlecompound. M.p. 124-125° C.; Retention Time HPLC 2.57 min; MS (ES+) 196(M+H⁺).

Step B: Preparation ofN-(4-Fluoro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy-piperidin-4-yl}-phenyl)-2,2-dimethyl-propionamide

A solution of n-buthyllithium in hexane (80.0 ml of a 1.6 M solution)was added dropwise to a solution ofN-(4-fluoro-phenyl)-2,2-dimethyl-propionamide (10.0 g) in dry THF (200ml) at −5° C. under a N2 atmosphere over 15 min. The resulting solutionwas stirred at 0° C. for 2 hours, and then a solution of1-benzyl-piperidin-4-one (9.20 ml) in THF (20 ml) was added dropewise tothe above solution of the dianion at 0° C. over a 1 hour period. Thereaction mixture was stirred for 2 hours at 0° C. and then overnight atr.t. The solution was the poured into ice water, made acidic with conc.HCl and extracted with ethyl acetate. The water layer was made basic andextracted three times with ethyl acetate. The combined organic layerswere washed with water, dried over sodium sulfate and concentrated invacuo. The residue was subjected to silica gel chromatography(hexane:ethyl acetate:triethyl amine 49:49:2) to afford the titleproduct (8.3 g). M.p. 172-173° C.; Retention Time HPLC 1.47 min; MS(ES+) 385 (M+H⁺).

EXAMPLE 13

This Example illustrates the preparation ofN-[2-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-fluoro-phenyl]-2,2-dimethyl-propionamide

A solution ofN-(4-fluoro-2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-4-hydroxy-piperidin-4-yl}-phenyl)-2,2-dimethyl-propionamide(4.00 g) in conc HCl (2.4 ml) and conc. AcOH (30 ml) was heated toreflux temperature for 24 hours. Then, water was added and the mixtureextracted three times with CH₂Cl₂, the combined organic layers weredried over sodium sulfate and concentrated in vacuo. The residue wasdissolved in CH₂Cl₂ (30 ml) and treated with triethylamine (2.8 ml) and2,2-dimethyl-propionyl chloride (0.61 ml). The resulting solution wasstirred at r.t. for 2 hour, then water was added and the mixtureextracted three times with ethyl acetate. The combined organic layerswere dried over sodium sulfate and concentrated in vacuo. The residuewas subjected to silica gel chromatography (hexane:ethylacetate:triethyl amine 79:19:2) to afford the title product (3.1 g).Viscous oil; Retention Time HPLC 2.00 min; MS (ES+) 367 (M+H⁺).

EXAMPLE 14

This Example illustrates the preparation ofN-(4-Fluoro-2-piperidin-4-yl-phenyl)-2,2-dimethyl-propionamide

A suspension ofN-[2-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-fluoro-phenyl]-2,2-dimethyl-propionamide(500 mg) and 10% Pd—C (50 mg) in EtOH (50 ml) was stirred in a H₂atmosphere for 16 hours. Then, the mixture was filtered and theresulting solution concentrated in vacuo to afford the title compound(380 mg). Viscous oil; Retention Time HPLC 1.61 min; MS (ES+) 279(M+H⁺).

EXAMPLE 15

This Example illustrates the preparation ofN-(2-{1-[(E)-3-(4-Chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenyl)-2,2-dimethyl-propionamide

N-(4-Fluoro-2-piperidin-4-yl-phenyl)-2,2-dimethyl-propionamide (380 mg)was dissolved in CHCl₃ (20 ml) and treated with triethyl amine (0.260mg). Then, a solution of 1-((E)-3-chloro-propenyl)-4-chloro-benzene (255mg) was added. After stirring for 16 hours at r.t. the mixture wasfiltrated and concentrated in vacuo. The residue was subjected to silicagel chromatography (hexane:ethyl acetate:triethyl amine 74:24:2) toafford the title product (380 mg). M.p. 174-176° C.; Retention Time HPLC2.37 min; MS (ES+) 4.29 (M+H⁺).

EXAMPLE 16

This Example illustrates the preparation of2-{1-[(E)-3-(4-Chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenylamine

A solution ofN-(2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenyl)-2,2-dimethyl-propionamide(315 mg) in 6N HCl (25 ml) and conc. AcOH (25 ml) was heated to refluxtemperature for 20 hours. Then, the solution was made basic (pH=12) bythe addition of solid NaOH, and extracted three times with CH₂Cl₂. Thecombined organic layers were dried over sodium sulfate and concentratedin vacuo. The residue was subjected to silica gel chromatography(hexane:ethyl acetate:triethyl amine 79:19:2) to afford the titleproduct (201 mg). M.p. 93-94° C.; Retention Time HPLC 2.18 min; MS (ES+)345 (M+H⁺).

EXAMPLE 17

This Example illustrates the preparation of2-Chloro-N-(2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenyl)-isonicotinamide

To a solution of2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenylamine(40 mg) and triethylamine (0.025 ml) in CHCl₃ (10 ml) were added2-chloro-isonicotinoyl chloride (1.2 equivalents; as a 1.0 M solution inCH₂Cl₂) over a 10 minute period. The resulting solution was stirred atr.t. over night, poured into saturated aqueous NaHCO₃ solution and themixture extracted three times with CH₂Cl₂. The combined organic layerswere dried over sodium sulfate and concentrated in vacuo. The residuewas subjected to silica gel chromatography (ethyl acetate:methanol 9:1)to afford the title product (43 mg). White solid; Retention Time HPLC2.36 min; MS (ES+) 486, 484 (M+H⁺). According to this method thefollowing compounds have been prepared starting from2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenylamine:

2,6-Dichloro-N-(2-{1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenyl)-isonicotinamide

White solid; Retention Time HPLC 2.67 min; MS (ES+) 520, 518 (M+H⁺).

N-(2-{1-[(E)-3-(4-Chloro-phenyl)-allyl]-piperidin-4-yl}-4-fluoro-phenyl)-isonicotinamide

White solid; Retention Time HPLC 2.07 min; MS (ES+) 450 (M+H⁺).

EXAMPLE 18

This Example illustrates the preparation of4-(5-Amino-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

A solution of 2-cyanoethyl hydrazine (5.1 g) in absolute ethanol (20 ml)was added dropwise to a solution of N-BOC-piperidone (12 g) in absoluteethanol at room temperature. The resulting solution was stirred at roomtemperature for 1 hour then the solvent was removed in vacuo. Theresulting oil was then added to a solution of sodium butoxide (preparedfrom 2.8 g of sodium and 60 ml of n-butanol) and the reaction mixturewas refluxed for 3 hours, cooled to room temperature, washed withsaturated aqueous ammonium chloride then with water, and the solvent wasremoved in vacuo. Precipitation from hexane afforded the title compound(11.5 g) as a yellow powder. M.p. 145-147° C.; ¹H NMR (400 MHz, CDCl₃)1.5 (s, 9H), 1.9 (m, 2H), 2.1 (m, 2H), 2.9 (m, 2H), 3.5 (m, 2H), 4.0 (m,1H), 4.2 (m, 2H), 5.5 (s, 1H), 7.3 (s, 1H).

EXAMPLE 19

This Example illustrates the preparation of4-{5-[(2-Chloro-pyridine-4-carbonyl)-amino]-pyrazol-1-yl}-piperidine-1-carboxylicacid tert-butyl ester

Triethylamine (2.8 ml) was added to a stirred solution of the compoundobtained in example 18 (2.66 g) in dichloromethane (100 ml); thesolution was cooled to 0° C. and 2-chloroisonicotinoyl chloride(prepared from 2.05 g of 2-chloroisonicotinic acid and 1.46 ml of oxalylchloride in 50 ml dichloromethane) was added. The resulting mixture wasstirred at room temperature for 12 hours, poured into water, extractedtwo times with dichloromethane; the combined organic layers were driedover sodium sulfate and concentrated in vacuo. The residue wasprecipitated from ethyl acetate/hexane to afford the title compound as apale yellow powder (3.4 g). M.p. 209-210° C.; ¹H NMR (400 MHz, CDCl₃)1.5 (s, 9H), 1.9 (m, 2H), 2.1 (m, 2H), 2.9 (m, 2H), 3.5 (m, 2H), 4.0 (m,1H), 4.2 (m, 2H), 6.1 (s, 1H), 7.5 (s, 1H), 7.6 (m, 1H), 7.7 (s, 1H),8.2 (sm, 1H), 8.5 (d, J=6 Hz, 1H).

EXAMPLE 20

This Example illustrates the preparation of2-Chloro-N-(2-{1-[3-(4-chloro-phenyl)-allyl]-piperidin-4-yl}-2H-pyrazol-3-yl)-isonicotinamide

A solution of the compound obtained in in Example 19 (2.7 g) indichloromethane (150 ml) was treated with trifluoroacetic acid (3.8 ml)for 6 hours at room temperature and the solvent was removed in vacuo.The residue was dissolved in acetonitrile (100 ml),N,N-diisopropylethylamine (9 ml) and 4-chlorocinnamyl chloride (1.9 g)were added. The resulting solution was stirred for 24 hours at roomtemperature, the solvent was removed in vacuo and the residue wassubjected to silica gel chromatography (ethyl acetate:methanol 95:5) toafford a product identified as2-{1-[3-(4-Chloro-phenyl)-allyl]-piperidin-4-yl}-2H-pyrazol-3-ylamine.This product was re-acylated using 1.05 g of 2-chloroisonicotinoylchloride, 0.7 ml of triethylamine in 50 ml dichloromethane according tothe method described in Step B. Silica gel chromatography of the residue(ethyl acetate:methanol 95:5) finally afforded the title product (370mg). M.p. 69-70° C. ¹H NMR (400 MHz, CDCl₃) 1.9-2.4 (m, 6H), 3.0 (d,J=11.6 Hz, 2H), 3.1 (d, J=6.4 Hz, 2H), 3.9 (m, 1H), 6.2 (m, 2H), 6.5 (d,J=16.0 Hz, 1H), 7.3 (m, 4H), 7.5 (s, 1H), 7.6 (s, 1H), 7.7 (br s, 1H),8.6 (d, J=4.8 Hz, 1H). Retention Time HPLC 2.32 min; MS (ES+) 456/458(M+H⁺).

The invention is further illustrated by the following Examples applyingcross coupling reactions.

EXAMPLE 21

This Example illustrates the preparation of2-Chloro-N-{1′-[(E)-3-(4-chloro-phenyl)-allyl]-1′,2′,3′,4′,5′,6′-hexahydro-[2,4]bipyridinyl-3-yl}-isonicotinamide.

Step A:1-(t-Butoxycarbonyl)-4-tributylstannyl-1,2,3,6-tetrahydropyridine (2.12g, prepared in 2 steps from 1-(t-butoxycarbonyl)-piperidin-4-oneaccording to WO 0123381) was dissolved in toluene (45 ml) in a dried,nitrogen-flushed flask. 2-Chloro-3-nitropyridine (712 mg) and palladiumtetrakis(triphenylphosphine) (130 mg) were added and the solution washeated at 110° C. for 16 hours. The reaction mixture was cooled to roomtemperature, the solvent removed in vacuo and the residue partitionedbetween ethyl acetate (100 ml) and NaOH 2N (100 ml). After 30 minstirring at room temperature, the organic layer was separated, washedwith NaOH 2N then water, dried over sodium sulfate and concentrated invacuo. The residue was subjected to silica gel chromatography (ethylacetate:cyclohexane 3:7) to afford3-nitro-3′,6′-dihydro-2′H-[2,4]bipyridinyl-1′-carboxylic acid tert-butyl(1.1 g) as light yellow crystals. M.p. 104-105° C.; ¹H NMR (400 MHz,CDCl₃) 1.4 (s, 9H), 2.5 (m, 2H), 3.6 (m, 2H), 4.0 (m, 2H), 5.9 (m, 1H),7.3 (dd, J=4.8, 8.4 Hz, 1H), 8.0 (d, J=8.4 Hz, 1H), 8.7 (d, J=4.8 Hz,1H); MS (ES+) 206 (MH+-BOC), 248 (MH+-isoprene).

Step B: Hydrazine monohydrate (0.4 ml) was added to a suspension ofRaney nickel (50% slurry in water, 200 mg) and the product obtained inStep A (240 mg) in ethanol (10 ml). After 4 hours stirring, the reactionmixture was filtered over Hyflo and the solvent removed in vacuo. Theresidue was dissolved in ethyl acetate, dried over sodium sulfate,filtered and concentrated in vacuo to afford3-amino-3′,6′-dihydro-2′H-[2,4]bipyridinyl-1′-carboxylic acid tert-butylester (200 mg) as white crystals. M.p. 104-105° C.; ¹H NMR (400 MHz,CDCl₃) 1.4 (s, 9H), 2.5 (m, 2H), 3.6 (m, 2H), 3.7 (brs, 2H), 4.0 (m,2H), 5.9 (m, 1H), 6.9 (m, 2H), 8.0 (m, 1H); MS (ES+) 176 (MH+-BOC), 220(MH+-isoprene), 276 (MH+).

Step C: The product obtained in Step B (815 mg) was reduced by transferhydrogenation using 10% Pd/C (200 mg) and ammonium formate (935 mg) inethanol (40 ml) at 60° C. for 45 min. After filtration over Hyflo, thesolvent was removed in vacuo. The residue was portioned between ethylacetate and water, the organic layer separated, washed with water, driedover sodium sulfate and concentrated in vacuo to give3-amino-3′,4′,5′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acidtert-butyl ester (785 mg) as an oil. ¹H NMR (400 MHz, CDCl₃) 1.4 (s,9H), 1.6 (m, 4H), 2.7 (m, 3H), 3.5 (brs, 2H), 4.0 (m, 2H), 6.9 (m, 2H),8.0 (m, 1H); MS (ES+) 178 (MH+-BOC), 222 (MH+-isoprene), 278 (MH⁺).

Step D: sodium bicarbonate (714 mg) was added to a stirred solution ofthe compound obtained in Step C (785 mg) in dichloromethane (30 ml); thesolution was then treated with 2-chloro-isonicotinoyl chloride (500 mg)and the resulting mixture was stirred at room temperature for 1 hour,poured into water, extracted two times with dichloromethane, thecombined organic layers were dried over sodium sulfate and concentratedin vacuo to afford3-[(2-Chloro-pyridine-4-carbonyl)-amino]-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylicacid tert-butyl ester (1.2 g).

Step E: A solution of the compound obtained in Step D (834 mg) indichloromethane (40 ml) was treated with trifluoroacetic acid (4 ml) for5 hours at room temperature. The reaction mixture was concentrated invacuo and then dried under high vacuum for 1 hour. The residue wasdissolved in acetonitrile (40 ml), diisopropylethylamine (1.8 ml) and4-chlorocinnamyl chloride (380 mg) were added. The solution was stirred20 hours at room temperature, the solvent was removed in vacuo and theresidue was subjected to silica gel chromatography (ethylacetate:methanol 95:5) to afford the title product (409 mg) as a yellowsolid. M.p. 78-80° C.; ¹H NMR (400 MHz, CDCl₃) 1.9 (m, 2H), 2.2 (m, 4H),2.8 (m, 1H), 3.2 (d, J=9 Hz, 2H), 3.3 (m, 2H), 6.2 (dt, J=18, 9 Hz, 1H),6.5 (d, J=18 Hz, 1H), 7.1-7.3 (m, 5H), 7.6 (d, J=4.4 Hz, 1H), 7.7 (s,1H), 7.9 (m, 1H, NH), 8.0 (d, J=7.6 Hz, 1H), 8.6 (d, J=3.6 Hz, 1H), 8.7(d, J=5.5 Hz, 1H); Retention Time HPLC 1.53 min; MS (ES+) 467/469(M+H⁺).

EXAMPLE 22

This Example illustrates the preparation of2-Chloro-N-{1′-[(E)-3-(4-chloro-phenyl)-allyl]-1′,2′,3′,6′-hexahydro-[2,4]bipyridinyl-3-yl}-isonicotinamide.

3-amino-3′,6′-dihydro-2′H-[2,4]bipyridinyl-1′-carboxylic acid tert-butylester (Example 1, Step B, 205 mg) was treated as described in Example 1,steps D and E to afford the title product (182 mg) as a yellow solid.M.p. 75-77° C.; ¹H NMR (400 MHz, CDCl₃) 1.8 (m, 2H), 2.7 (m, 2H), 2.8(m, 2H), 3.2 (m, 2H), 3.3 (m, 2H), 6.0 (s, 1H), 6.2 (dt, J=18, 9 Hz,1H), 6.5 (d, J=18 Hz, 1H), 7.1-7.3 (m, 6H), 7.6 (m, 1H), 7.7 (s, 1H),7.7 (s, 1H), 8.3 (d, J=3.6 Hz, 1H), 8.5 (d, J=5.5 Hz, 1H), 8.8 (m, 1H,NH); Retention Time HPLC 1.51 min; MS (ES+) 465/467 (M+H⁺).

The following compounds were prepared according to procedures analogousto those described in Example 22:

Retention M.p Time Compound Name Structure (° C.) MH⁺ (min)2-chloro-N-{1′- [(E)-3-(4-chloro- phenyl)-allyl]- 1′,2′,3′,6- hexahydro-[2,4′]bipyridinyl-3- yl}- isonicotinamide

499/501/503 1.64

EXAMPLE 23

This Example illustrates the preparation of2-Chloro-N-{5-chloro-1′-[(E)-3-(4-chloro-phenyl)-allyl]-1′,2′,3′,4′,5′,6′-hexahydro-[2,4]bipyridinyl-3-yl}-isonicotinamide.

A mixture of trimethylchlorosilane and 1,2-dibromoethane (7:5 v/v, 0.125ml) was added dropwise (keeping the T° C. below 50° C.) to a suspensionof zinc powder (422 mg) in dimethylacetamide (3 ml). The mixture wasstirred 20 min at room temperature then a solution of1-(t-butoxycarbonyl)-4-iodo-piperidine (1.62 g, prepared in 2 steps from1-(t-butoxycarbonyl)-piperidin-4-one according to J. Org. Chem. 2004,5120) in dimethylacetamide (3 ml) was added dropwise over 5 min(slightly exothermic). The resulting mixture was stirred at roomtemperature for 30 min then cannulated into a mixture of2,5-dichloro-3-aminopyridine (603 mg), copper(I) iodide (42 mg) andPdCl2(dppf) (91 mg) in dimethylacetamide (5 ml). The resulting mixturewas stirred at 80° C. for 3 hours, cooled to room temperature, pouredinto water, extracted with ethyl acetate, dried over sodium sulfate andconcentrated in vacuo. The residue was subjected to silica gelchromatography (ethyl acetate:cyclohexane 3:7) to afford3-amino-5-chloro-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acidtert-butyl ester (535 mg) as a yellow solid. ¹H NMR (400 MHz, CDCl₃) 1.4(s, 9H), 1.8 (m, 4H), 2.6 (m, 1H), 2.8 (m, 2H), 3.7 (br s, 2H), 4.2 (m,2H), 6.9 (s, 1H), 7.9 (s, 1H).

The product thus obtained (448 mg) was treated as described in Example1, Steps D and E to afford the title product (455 mg) as a white solid.M.p. 63-67° C.; ¹H NMR (400 MHz, CDCl₃) 1.9 (m, 2H), 2.2 (m, 4H), 2.7(m, 1H), 3.2 (m, 2H), 3.3 (m, 2H), 6.2 (dt, J=18, 9 Hz, 1H), 6.5 (d,J=18 Hz, 1H), 7.1-7.3 (m, 4H), 7.7 (d, J=5.2 Hz, 1H), 7.8 (s, 1H), 7.9(m, 1H, NH), 8.3 (d, J=2.4 Hz, 1H), 8.4 (d, J=2.4 Hz, 1H), 8.6 (d, J=4.8Hz, 1H), 8.7 (d, J=5.5 Hz, 1H); Retention Time HPLC 1.53 min; MS (ES+)501/503/505 (M+H⁺).

The following compounds were prepared according to procedures analogousto those described in Example 23:

Retention M.p Time Compound Name Structure (° C.) MH⁺ (min)2-chloro-N-{4- chloro-1′-[(E)-3-(4- chloro-phenyl)-allyl]-1′,2′,3′,4′,5′,6′- hexahydro- [2,4′]bipyridinyl-3-yl}-isonicotinamide

80-85 499/501/503 1.55 N-(5-bromo-3-{1- [(E)-3-(4-chloro-phenyl)-allyl]- piperidin-4-yl}- pyrazin- 2-yl)-2-chloro-isonicotinamide

548/550 1.33

The following compounds (Tables EX23.1-EX23.11) were prepared applyingSuzuki cross coupling reactions as described in Schemes 8-13. Reactionconditions described in the literature [P. R Eastwood, THL 41, 3705(2000) for example] or as described above were applied.

TABLE EX23.1

Re- ten- Com- tion pound Mp MH⁺- time No R⁸ S₃ S₄ S₅ S₆ (° C.) BOC (min)EX23-1- BOC H H F H 323/322 2.22 2 EX23-1- BOC H H CF₃ H 373/372 2.30 3EX23-1- BOC H H OCH₃ H 235/234 2.23 4 EX23-1- BOC CH₃ H H H 219/220 2.195 EX23-1- BOC H H H CH₃ 100- 219/220 2.22 6 102 EX23-1- BOC H H COOCH₃ H263/264 2.08 7

TABLE EX23.2

Com- Retention pound Mp MH⁺- time No R⁸ S₃ S₄ S₅ S₆ (° C.) BOC (min)EX23-2-1 BOC H H H F 100-102  19/3194 2.15 EX23-2-2 BOC H F H F 211/2102.12 EX23-2-3 BOC H i-Pr H H 217/216 2.11 EX23-2-4 BOC H F F F 229/2302.21 EX23-2-5 BOC H OCF₃ H H 259/260 2.22 EX23-2-6 BOC H F H H 193/1942.02

TABLE EX23.3

Re- ten- Com- tion pound Mp MH⁺- time No R⁸ S₃ S₄ S₅ S₆ (° C.) BOC (min)EX23- BOC H H CH₃ H 191/ 1.90 3-1 192 EX23- BOC H H F H 195/ 2.05 3-2196 EX23- BOC H H CF₃ H 245/ 2.22 3-3 246 EX23- BOC H H OCH₃ H 207/ 1.923-4 208 EX23- BOC CH3 H H H 191/ 1.87 3-5 192 EX23- BOC H H H CH₃ 191/2.06 3-6 192 EX23- BOC H H COOCH₃ H 235/ 2.00 3-7 236 EX23- BOC H H H F123- 195/ 2.12 3-8 126 196 EX23- BOC H F H F 213/ 2.10 3-9 214 EX23- BOCH i-Pr H H 219/ 2.00 3-10 220 EX23- BOC H F F F 231/ 2.16 3-11 232 EX23-BOC H OCF₃ H H 261/ 2.18 3-12 262 EX23- BOC H F H H 195/ 1.87 3-13 196

TABLE EX23.4

Compound Mp MH⁺- Retention No R⁸ S₃ S₄ S₅ S₆ (° C.) BOC time (min)EX23-4-1 BOC H H CH₃ H amorph 330/332/333 2.14 EX23-4-2 BOC H H F Hamorph 334/336/337 2.11 EX23-4-3 BOC H H CF₃ H amorph 384/386/387 2.22EX23-4-4 BOC H H OCH₃ H amorph 346/348/349 2.07 EX23-4-5 BOC CH₃ H H Hamorph 330/332/333 2.04 EX23-4-6 BOC H H H CH₃ 330/332/333 2.06 EX23-4-7BOC H H COOCH₃ H amorph 374/376/377 2.05 EX23-4-8 BOC H H H F amorph334/336/337 2.02 EX23-4-9 BOC H F H F amorph 352/354/355 2.08 EX23-4-10BOC H i-Pr H H amorph 358/360/361 2.25 EX23-4-11 BOC H F F F amorph370/372/372 2.25 EX23-4-12 BOC H OCF₃ H H 227-230 400/402/403 2.22

TABLE EX23.5

Compound Retention No R⁸ S₃ S₄ S₅ S₆ Mp (° C.) MH⁺ time (min) EX23-5-1 HH H CH₃ H amorph 330/332/333 1.17 EX23-5-2 H H H F H amorph 334/336/3371.18 EX23-5-3 H H H CF₃ H amorph 384/386/387 1.35 EX23-5-4 H H H OCH₃ Hamorph 346/348/349 1.17 EX23-5-5 H CH₃ H H H amorph 330/332/333 1.12EX23-5-6 H H H H CH3 amorph 330/332/333 1.15 EX23-5-7 H H H COOCH₃ Hamorph 374/376/377 1.13 EX23-5-8 H H H H F amorph 334/336/337 1.14EX23-5-9 H H F H F amorph 352/354/355 1.22 EX23-5-10 H H i-Pr H H amorph358/360/361 1.37 EX23-5-11 H H F F F amorph 370/372/372 1.28 EX23-5-12 HH OCF₃ H H amorph 400/402/403 1.30

TABLE EX23.6

Compound Mp Retention No R⁸ S₃ S₄ S₅ S₆ (° C.) MH⁺ time (min) EX23-6-14-chlorocinnamyl H H CH₃ H 203-206 480/482/483 1.51 EX23-6-24-chlorocinnamyl H H F H 484/486/487 1.49 EX23-6-3 4-chlorocinnamyl H HCF₃ H 534/536/537 1.59 EX23-6-4 4-chlorocinnamyl H H OCH₃ H 496/498/4991.47 EX23-6-5 4-chlorocinnamyl CH₃ H H H amorph 480/482/483 1.49EX23-6-6 4-chlorocinnamyl H H H CH₃ 90-93 480/482/483 1.54 EX23-6-74-chlorocinnamyl H H COOCH₃ H 92-95 524/526/527 1.52 EX23-6-84-chlorocinnamyl H H H F 484/486/487 1.44 EX23-6-9 4-chlorocinnamyl H FH F 221-223 502/504/505 1.49 EX23-6-10 4-chlorocinnamyl H i-Pr H Hamorph 508/510/511 1.61 EX23-6-11 4-chlorocinnamyl H F F F amorph520/522/523 1.53 EX23-6-12 4-chlorocinnamyl H OCF₃ H H 550/552/553 1.61EX23-6-13 4-chlorocinnamyl H F H H 165-167 484/486/487 1.49

TABLE EX23.7

Com- Retention pound Mp time No R⁸ S₃ S₄ S₅ S₆ (° C.) MH⁺-BOC (min)EX23-7-1 BOC H F H F amorph 350/352/353 2.07 EX23-7-2 BOC H i-Pr H H167-169 356/358/359 2.27 EX23-7-3 BOC H F F F 169-171 368/370/371 2.13EX23-7-4 BOC H OCF₃ H H amorph 398/400/401 2.23 EX23-7-5 BOC H F H Hamorph 332/334/335 2.12

TABLE EX23.8

Compound Mp Retention No R⁸ S₃ S₄ S₅ S₆ (° C.) MH⁺ time (min) EX23-8-1 HH F H F EX23-8-2 H H i-Pr H H amorph 356/358/359 1.33 EX23-8-3 H H F F FEX23-8-4 H H OCF₃ H H amorph 398/400/401 1.37 EX23-8-5 H H F H H amorph332/334/335 1.09

TABLE EX23.9

Retention Compound Mp time No R⁸ S₃ S₄ S₅ S₆ (° C.) MH⁺ (min) EX23-9-14-chlorocinnamyl H F H F EX23-9-2 4-chlorocinnamyl H i-Pr H H amorph506/508/509 1.67 EX23-9-3 4-chlorocinnamyl H F F F EX23-9-44-chlorocinnamyl H OCF₃ H H 548/550/551 1.66 EX23-9-5 4-chlorocinnamyl HF H H amorph 482/484/485 1.47

TABLE EX23.10

Retention Compound Mp time No R⁸ T₁ T₂ T₃ T₄ (° C.) MH⁺ (min) EX23-10-14-chlorocinnamyl N C—Me CH CH 420/422 1.27 EX23-10-2 4-bromocinnamyl NC—Me CH CH 525/526 1.29 EX23-10-3 4-chlorocinnamyl N C—Br CH N 546/5481.37 EX23-10-4 4-chlorocinnamyl CH N C—Cl N 502/504 1.30 EX23-10-54-chlorocinnamyl C—Cl N CH CH 501/503 1.54 EX23-10-6 4-chlorocinnamylC—Cl N C—Cl CH 535/537 1.63 EX23-10-7 4-chlorocinnamyl CH C—CF₃ CH N533/535 1.39 EX23-10-8 4-chlorocinnamyl N C—Cl CH CH 501/503 1.34EX23-10-9 4-bromocinnamyl N C—Cl CH CH 545/547 1.36 EX23-10-104-chlorocinnamyl S CH CH — 470/472 1.38 EX23-10-11 4-chlorocinnamyl SC—Cl CH — 506/508 1.43

TABLE EX23.11

Compound Mp Retention No R⁸ T₁ T₂ T₃ T₄ (° C.) MH⁺ time (min) EX23-11-14-chlorocinnamyl N C—Me CH CH 481/483 1.33 EX23-11-2 4-bromocinnamyl NC—Me CH CH 527/529/530 1.33 EX23-11-3 4-chlorocinnamyl CH CF₃ CH N535/537 1.35 EX23-11-4 4-bromocinnamyl CH CF₃ CH N 581/582.5 1.36

EXAMPLE 24

This Example illustrates the pesticidal/insecticidal properties ofcompounds of formula (I). Test against were performed as follows:

Spodoptera littoralis (Egyptian Cotton Leafworm)

Cotton leaf discs were placed on agar in a 24-well microtiter plate andsprayed with test solutions at an application rate of 200 ppm. Afterdrying, the leaf discs were infested with 5 L₁ larvae. The samples werechecked for mortality, repellent effect, feeding behaviour, and growthregulation 3 days after treatment (DAT). The following compounds gave atleast 80% control of Spodoptera littoralis: Iaaa-3 and Iaaa-49.

Heliothis virescens (Tobacco Budworm):

Eggs (0-24 h old) were placed in 24-well microtiter plate on artificialdiet and treated with test solutions at an application rate of 200 ppmby pipetting. After an incubation period of 4 days, samples were checkedfor egg mortality, larval mortality, and growth regulation. Thefollowing compounds gave at least 80% control of Heliothis virescen:Ia-49, Ia-50, Ia-53, Iaaa-3, Iaaa-26, Iaaa-49, Iaaa-52, Iaab-26 andIaac-26.

Plutella xylostella (Diamond Back Moth):

24-well microtiter plate (MTP) with artificial diet was treated withtest solutions at an application rate of 18.2 ppm by pipetting. Afterdrying, the MTP's were infested with larvae (L2) (10-15 per well). Afteran incubation period of 5 days, samples were checked for larvalmortality, antifeedant and growth regulation. The following compoundsgave at least 80% control of Plutella xylostella: Ia-49, Ia-53, Iaaa-3,Iaaa-26, Iaaa-49 and Iaac-26.

Aedes aegypti (Yellow Fever Mosquito):

10-15 Aedes larvae (L2) together with a nutrition mixture are placed in96-well microtiter plates. Test solutions at an application rate of 2ppm are pipetted into the wells. 2 days later, insects were checked formortality and growth inhibition. The following compounds gave at least80% control of Aedes aegypti: Ia-53, Iaaa-3, Iaaa-26, Iaaa-49, Iaaa-52,Iaab-26, Iaac-26 and Iaai-26.

1. A method of combating and controlling insects, acarines, nematodes ormolluscs which comprises applying to a pest, to a locus of a pest, or toa plant susceptible to attack by a pest an insecticidally, acaricidally,nematicidally or molluscicidally effective amount of a compound offormula I

where Y is a single bond, C═O, C═S or S(O)_(m) where m is 0, 1 or 2; thering

is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromaticring; Z and Z′ are joined by a single or a double bond and are

provided that both are not N; R¹ is hydrogen, optionally substitutedalkyl, optionally substituted alkoxycarbonyl, optionally substitutedalkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl,optionally substituted dialkylaminocarbonyl, optionally substitutedaryl, optionally substituted heteroaryl, optionally substituted alkoxy,optionally substituted aryloxy, optionally substituted heteroaryloxy,optionally substituted heterocyclyloxy, cyano, optionally substitutedalkenyl, optionally substituted alkynyl, optionally substitutedcycloalkyl, optionally substituted cycloalkenyl, formyl, optionallysubstituted heterocyclyl, optionally substituted alkylthio, NO orNR¹³R¹⁴ where R¹³ and R¹⁴ are independently hydrogen, COR¹⁵, optionallysubstituted alkyl, optionally substituted aryl, optionally substitutedheteroaryl, optionally substituted heterocyclyl or R¹³ and R¹⁴ togetherwith the N atom to which they are attached form a group—N═C(R¹⁶)—NR¹⁷R¹⁸ or R¹³ and R¹⁴ together with the N atom to which theyare attached form a five, six or seven-membered heterocyclic ring whichmay contain one or two further heteroatoms selected from O, N or S andwhich may be optionally substituted by one or two C₁₋₆ alkyl groups; R¹⁵is H, optionally substituted alkyl, optionally substituted alkoxy,optionally substituted aryl, optionally substituted aryloxy optionallysubstituted heteroaryl, optionally R¹⁹ substituted heteroaryloxy orNR¹⁹R²⁰; R¹⁶, R¹⁷ and R¹⁸ are each independently H or lower alkyl; R¹⁹and R²⁰ are independently optionally substituted alkyl, optionallysubstituted aryl or optionally substituted heteroaryl; R² is H, hydroxy,optionally substituted alkoxy or optionally substituted alkyl; or R¹ andR² together with the groups Y and N form a 5- or 6-membered heterocyclicring which may optionally contain one further heteroatom selected fromO, N or S and which may be optionally substituted by C₁₋₄ alkyl, C₁₋₄haloalkyl or halogen; R³ is H, OH, halogen or optionally substitutedalkyl; R^(3a) is H or R³ and R^(3a) together form a bond; each R⁴ isindependently halogen, nitro, cyano, optionally substituted C₁₋₈ alkyl,optionally substituted C₂₋₆ alkenyl, optionally substituted C₂₋₆alkynyl, optionally substituted alkoxycarbonyl, optionally substitutedalkylcarbonyl, optionally substituted alkylaminocarbonyl, optionallysubstituted dialkylaminocarbonyl, optionally substituted C₃₋₇cycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, optionally substituted heterocyclyl, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitutedheteroaryloxy, optionally substituted alkylthio or R²¹R²²N where R²¹ andR²² are, independently, hydrogen, C₁₋₈ alkyl, C₃₋₇ cycloalkyl, C₃₋₆alkenyl, C₃₋₆ alkynyl, C₃₋₇ cycloalkyl(C₁₋₄)alkyl, C₂₋₆ haloalkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, C₁₋₆ alkoxycarbonyl or R²¹ and R²² together with theN atom to which they are attached form a five, six or seven-memberedheterocyclic ring which may contain one or two further heteroatomsselected from O, N or S and which may be optionally substituted by oneor two C₁₋₆ alkyl groups, or 2 adjacent groups R⁴ together with thecarbon atoms to which they are attached form a 4, 5, 6, or 7 memberedcarbocyclic or heterocyclic ring which may be optionally substituted byhalogen; n is 0, 1, 2, 3 or 4; R⁸ is optionally substituted alkyl,optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted cycloalkyl, optionally substituted aryl,optionally substituted alkoxy, optionally substituted aryloxy,optionally substituted alkoxycarbonyl, optionally substitutedalkylcarbonyl or optionally substituted alkenylcarbonyl; each Ra isindependently halogen, hydroxy, cyano, optionally substituted C₁₋₈alkyl, optionally substituted C₂₋₆ alkenyl, optionally substituted C₂₋₆alkynyl, optionally substituted alkoxycarbonyl, optionally substitutedalkylcarbonyl, optionally substituted alkylaminocarbonyl, optionallysubstituted dialkylaminocarbonyl, optionally substituted C₃₋₇cycloalkyl, optionally substituted aryl, optionally substitutedheteroaryl, optionally substituted heterocyclyl, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitutedheteroaryloxy, optionally substituted alkylthio, optionally substitutedarylthio or R²³R²⁴N where R²³ and R²⁴ are, independently, hydrogen, C₁₋₈alkyl, C₃₋₇ cycloalkyl, C₃₋₆ alkenyl, C₃₋₆ alkynyl, C₃₋₇cycloalkyl(C₁₋₄alkyl, C₂₋₆ haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₁₋₆alkoxycarbonyl or R²³ and R²⁴ together with the N atom to which they areattached form a five, six or seven-membered heterocyclic ring which maycontain one or two further heteroatoms selected from O, N or S and whichmay be optionally substituted by one or two C₁₋₆ alkyl groups, or two Ragroups attached to the same carbon atom are ═O, ═S, ═NRb, ═CRcRd whereRb, Rc and Rd are independently H or optionally substituted alkyl; p is0, 1, 2, 3 or 4 or salts or N-oxides thereof.
 2. A method according toclaim 1 wherein the ring

is a 6-membered aromatic ring or is 5 or 6 membered heteroaromatic ringwherein the ring members are each independently CH, S, N, NR⁴, O, or CR⁴provided that at least one ring member is other than CH or CR⁴ and thatthere are no more than one O or S atoms present in the ring.
 3. A methodaccording to claim 1 wherein Y is a single bond, C═O or C═S.
 4. A methodaccording to claim 1 wherein R¹ is hydrogen, C₁₋₆ alkyl, C₁₋₆cyanoalkyl, C₁₋₆ haloalkyl, C₃₋₇ cycloalkyl(C₁₋₄alkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, heteroaryl(C₁₋₆)alkyl (wherein the heteroaryl groupmay be optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆alkylcarbonylamino, arylcarbonyl, or two adjacent positions on theheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen), aryl(C₁₋₆)alkyl (wherein the aryl group may be optionallysubstituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylcarbonylamino, arylcarbonyl,or two adjacent positions on the aryl system may be cyclised to form a5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionallysubstituted with halogen), C₁₋₆ alkylcarbonylamino(C₁₋₆)alkyl, aryl(which may be optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl,C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the arylsystem may be cyclised to form a 5, 6 or 7 membered carbocyclic orheterocyclic ring, itself optionally substituted with halogen),heteroaryl (which may be optionally substituted by halo, nitro, cyano,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl,C₁₋₆ alkylcarbonylamino, arylcarbonyl, or two adjacent positions on theheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen), C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, phenoxy (wherein the phenylgroup is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy,C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino), heteroaryloxy (optionally substituted by halo, nitro,cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy),heterocyclyloxy (optionally substituted by halo, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), cyano, C₂₋₆ alkenyl, C₂₋₆alkynyl, C₃₋₆ cycloalkyl, C₅₋₇ cycloalkenyl, heterocyclyl (optionallysubstituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy or C₁₋₆ haloalkoxy), C₁₋₆ alkylthio, C₁₋₆ haloalkylthio orNR¹³R¹⁴ where R¹³ and R¹⁴ are independently hydrogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, phenyl (which may be optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino, dialkylamino or C₁₋₄alkoxycarbonyl), phenyl(C₁₋₆)alkyl (wherein the phenyl group may beoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacentpositions on the phenyl ring may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen), heteroaryl(C₁₋₆)alkyl (wherein the heteroaryl group maybe optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylsulfonyl, C₁₋₆alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl, C₁₋₆alkylcarbonylamino, arylcarbonyl, or two adjacent positions on theheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen) or heteroaryl (which may be optionally substituted by halo,nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆haloalkoxy, C₁₋₄ alkoxycarbonyl C₁₋₆ alkylcarbonylamino,phenyloxycarbonylamino (wherein the phenyl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino), amino,C₁₋₆ alkylamino or phenylamino (wherein the phenyl group is optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino)).
 5. Amethod according to claim 1 wherein R² is hydrogen, hydroxy, C₁₋₆ alkylor C₁₋₆ haloalkyl.
 6. A method according to claim 1 wherein each R⁴ isindependently halogen, cyano, C₁₋₈ alkyl, C₁₋₈ haloalkyl, C₁₋₆cyanoalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₃₋₇ cycloalkyl(C₁₋₆)alkyl, C₅₋₆cycloalkenyl(C₁₋₆)alkyl, C₃₋₆ alkenyloxy(C₁₋₆)alkyl, C₃₋₆alkynyloxy(C₁₋₆)alkyl, aryloxy(C₁₋₆)alkyl, C₁₋₆ carboxyalkyl, C₁₋₆alkylcarbonyl(C₁₋₆)alkyl, C₂₋₆ alkenylcarbonyl(C₁₋₆)alkyl, C₂₋₆alkynylcarbonyl(C₁₋₄-alkyl, C₁₋₆ alkoxycarbonyl(C₁₋₆)alkyl, C₃₋₆alkenyloxycarbonyl(C₁₋₆)alkyl, C₃₋₆ alkynyloxycarbonyl(C₁₋₆)alkyl,aryloxycarbonyl(C₁₋₆)alkyl, C₁₋₆ alkylthio(C₁₋₆)alkyl, C₁₋₆alkylsulfinyl(C₁₋₆)alkyl, C₁₋₆ alkylsulfonyl(C₁₋₆)alkyl,aminocarbonyl(C₁₋₆)alkyl, C₁₋₆ alkylaminocarbonyl(C₁₋₆)alkyl,di(C₁₋₆)alkylaminocarbonyl(C₁₋₆)alkyl, phenyl(C₁₋₄alkyl (wherein thephenyl group is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino), heteroaryl(C₁₋₄alkyl (wherein the heteroarylgroup is optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), heterocyclyl(C₁₋₄alkyl(wherein the heterocyclyl group is optionally substituted by halo,nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆haloalkoxy), C₂₋₆ alkenyl, aminocarbonyl(C₂₋₆)alkenyl, C₁₋₆alkylaminocarbonyl(C₂₋₆)alkenyl,di(C₁₋₆)alkylaminocarbonyl(C₂₋₆)alkenyl, phenyl(C₂₋₄)-alkenyl, (whereinthe phenyl group is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino), C₂₋₆ alkynyl, trimethylsilyl(C₂₋₆)alkynyl,aminocarbonyl(C₂₋₆)alkynyl, C₁₋₆ alkylaminocarbonyl(C₂₋₆)alkynyl,di(C₁₋₆)alkylaminocarbonyl(C₂₋₆)alkynyl, C₁₋₆ alkoxycarbonyl, C₃₋₇cycloalkyl, C₃₋₇ halocycloalkyl, C₃₋₇ cyanocycloalkyl, C₁₋₃alkyl(C₃₋₇)-cycloalkyl, C₁₋₃ alkyl(C₃₋₇)halocycloalkyl,phenyl(optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino), heteroaryl (optionally substituted by halo, nitro, cyano,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy),heterocyclyl (wherein the heterocyclyl group is optionally substitutedby halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆haloalkoxy), or 2 adjacent groups R⁴ together with the carbon atoms towhich they are attached form a 4, 5, 6 or 7 membered carbocylic orheterocyclic ring which may be optionally substituted by halogen, C₁₋₈alkoxy, C₁₋₆ haloalkoxy, phenoxy (optionally substituted by halo, nitro,cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy),heteroaryloxy (optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl,C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), C₁₋₈ alkylthio orR¹⁹R²⁰N where R¹⁹ and R²⁰ are, independently, hydrogen, C₁₋₈ alkyl, C₃₋₇cycloalkyl, C₃₋₆ alkenyl, C₃₋₆ alkynyl, C₂₋₆ haloalkyl, C₁₋₆alkoxycarbonyl or R¹⁹ and R²⁰ together with the N atom to which they areattached form a five, six or seven-membered heterocyclic ring which maycontain one or two further heteroatoms selected from O, N or S and whichmay be optionally substituted by one or two C₁₋₆ alkyl groups; n is 0,1, 2 or
 3. 7. A method according to claim 1 wherein R⁸ is C₁₋₁₀ alkyl,C₁₋₁₀ haloalkyl, aryl(C₁₋₆)alkyl (wherein the aryl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino),heteroaryl(C₁₋₆)alkyl (wherein the heteroaryl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino),arylcarbonyl-(C₁₋₆)alkyl (wherein the aryl group may be optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino and thealkyl group may be optionally substituted by aryl), C₂₋₈ alkenyl, C₂₋₈haloalkenyl, aryl(C₂₋₆)-alkenyl (wherein the aryl group is optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino, C₁₋₆alkoxycarbonyl, or two adjacent substituents can cyclise to form a 5, 6or 7 membered carbocyclic or heterocyclic ring),heteroaryl(C₂₋₆)-alkenyl (wherein the heteroaryl group is optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino, C₁₋₆alkoxycarbonyl, or two adjacent substituents can cyclise to form a 5, 6or 7 membered carbocyclic or heterocyclic ring), C₂₋₆ alkynyl,phenyl(C₂₋₆)alkynyl (wherein the phenyl group is optionally substitutedby halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy,CN, NO₂, aryl, heteroaryl, amino or dialkylamino), C₃₋₇ cycloalkyl, C₁₋₆alkoxycarbonyl, C₁₋₆ alkylcarbonyl, C₁₋₆ haloalkylcarbonyl oraryl(C₂₋₆)alkenylcarbonyl (wherein the aryl group may be optionallysubstituted halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino or dialkylamino), or—C(R⁵¹)(R⁵²)—[CR⁵³═CR⁵⁴]z-R⁵⁵ where z is 1 or 2, R⁵¹ and R⁵² are eachindependently H, halo or C₁₋₂ alkyl, R⁵³ and R⁵⁴ are each independentlyH, halogen, C₁₋₄ alkyl or C₁₋₄ haloalkyl and R⁵⁵ is optionallysubstituted aryl or optionally substituted heteroaryl.
 8. A methodaccording to claim 1 wherein Ra is independently halo, cyano, C₁₋₃alkyl, hydroxy or two Ra groups together with the carbon atom to whichthey are attached form ═O, ═S, ═NRb, ═CRcRd where Rb, Rc and Rd areindependently H or optionally substituted alkyl, and p is 0, 1 or
 2. 9.A method according to claim 1 wherein R³ is hydrogen, hydroxy, halogen,C₁₋₆ alkyl or C₁₋₆ haloalkyl and R^(3a) is hydrogen or R³ and R^(3a)together form a double bond.
 10. A compound of formula I′

wherein; the ring

and R¹, R², R³, R^(3a), R⁴, Ra, Y, n and p are as defined in relation toformula I in claim 1 and R⁸ is —C(R⁵¹)(R⁵²)—[CR⁵³═CR⁵⁴]z-R⁵⁵ where z is1 or 2, R⁵¹ and R⁵² are each independently H or C₁₋₂ alkyl, R⁵³ and R⁵⁴are each independently H, halogen, C₁₋₄ alkyl or C₁₋₄ haloalkyl and R⁵⁵is phenyl substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino ordialkylamino or heteroaryl substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino or dialkylamino or salts or N-oxides thereof.
 11. A compound offormula IIa

wherein; the ring

and R³, R^(3a), R⁴, R⁸, Ra, n and p are as defined in relation toformula I′ in claim 10 and R⁶⁰ is NH₂, NO₂ or halogen; or a compound offormula (IIb)

wherein; the ring

and R⁴, R⁶⁰ and n are as defined in relation to formula IIa, R³ andR^(3a) are both H or together form a bond and R⁸ is methyl, benzyl orCOOC₁₋₆alkyl provided that the compound is not tert-butyl4-(2-aminophenyl)piperidine-1-carboxylate or2,4-diamino-5-(1-benzyl-4-piperidinyl)-pyrimidine.
 12. An insecticidalacaricidal and nematicidal composition comprising an insecticidally,acaricidally or nematicidally effective amount of a compound of formulaI as defined in claim 1.